original_index int64 2 1.77M | extracted_from_file stringclasses 489
values | date_of_experiment timestamp[ns]date | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1
class | rxn_str stringlengths 87 6.12k | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 null | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | agent_003 null | agent_004 null | agent_005 null | agent_006 null | agent_007 null | agent_008 null | agent_009 null | agent_010 null | agent_011 null | agent_012 null | agent_013 null | agent_014 null | agent_015 null | agent_016 null | solvent_000 stringclasses 446
values | solvent_001 stringclasses 405
values | solvent_002 null | solvent_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null | temperature float64 -230 30.1k ⌀ | rxn_time float64 0 2.16k ⌀ | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 null | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
623,069 | ord_dataset-c9f990dde2dc45d0948ecbe037a0d819 | null | 2004-01-01T00:01:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[CH2:20][CH2:19][NH:18][CH2:17][C:16]2=[O:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[CH2:30][CH2:31][S:32](Cl)(=[O:34])=[O:33]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[CH2:20][CH2:19][N:18]([S:32]([CH:31]... | O=S(=O)(Cl)CCCl | CC(C)(C)OC(=O)N1CCC(CN2CCNCC2=O)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 0.5 | To a solution of 1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinone (5.0 g) and triethylamine (6.792 g) in dichloromethane (80 ml) was added dropwise at 0° C. a solution of 2-chloroethanesulfonyl chloride (4.11 g) in dichloromethane (20 ml), and the mixture was stirred at 0 for 30 minutes. The reaction solu... | C=CS(=O)(=O)N1CCN(CC2CCN(C(=O)OC(C)(C)C)CC2)C(=O)C1 | null | 61.2 | null |
1,280,742 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | C([O:3][C:4](=O)[CH2:5][C:6]([C@H:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH3:17])=[O:15])[C@@H:10]([CH2:18][C:19]2[CH:24]=[C:23]([F:25])[C:22]([F:26])=[C:21]([F:27])[CH:20]=2)[CH2:9]1)=[O:7])C.[OH-].[Na+].[NH2:31]O.Cl>CO.O>[O:3]=[C:4]1[CH:5]=[C:6]([C@H:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH3:17])=[O:15])[C@@H:10](... | NO | CCOC(=O)CC(=O)[C@H]1CCN(C(=O)OC)[C@@H](Cc2cc(F)c(F)c(F)c2)C1 | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | -40 | 0.33 | Cis-methyl 4-(3-ethoxy-3-oxopropanoyl)-2-(3,4,5-trifluorobenzyl)piperidine-1-carboxylate (1.967 g, 4.90 mmol) was dissolved in MeOH (20 mL) and cooled to −40° C. under nitrogen. Sodium hydroxide (1.290 mL, 4.90 mmol) in water (2.000 mL) was added and the mixture stirred at −40° C. for 20 min. Hydroxylamine (50% by weig... | COC(=O)N1CC[C@H](c2cc(=O)[nH]o2)C[C@@H]1Cc1cc(F)c(F)c(F)c1 | null | 74.6 | null |
874,649 | ord_dataset-e1c3af9b105b4af09a5171403bbfc06f | null | 2009-01-01T00:04:00 | true | [C:1]([N:4]1[CH:10]2[CH:8]([CH:9]2[C:11](OCC)=[O:12])[N:7]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[C:6](=[O:24])[CH2:5]1)(=[O:3])[CH3:2].[BH4-].[Na+].CO>CCO>[C:1]([N:4]1[CH:10]2[CH:8]([CH:9]2[CH2:11][OH:12])[N:7]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)[C:6](=[O:24])[CH2:5]1... | CCOC(=O)C1C2C1N(Cc1ccc(F)cc1)C(=O)CN2C(C)=O | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CCO | null | null | null | null | null | null | null | null | null | null | 8 | To a solution of the exo isomer of ethyl 5-acetyl-2-(4-fluorobenzyl)-3-oxo-2,5-diazabicyclo[4.1.0]heptane-7-carboxylate (3.3 g, 9.87 mmol) in 32 ml EtOH at room temperature was added sodium borohydride (398 mg, 10.5 mmol). After stirring overnight, the reaction mixture was treated with 200 mL MeOH, stirred for 1 h and ... | CC(=O)N1CC(=O)N(Cc2ccc(F)cc2)C2C(CO)C21 | null | null | null |
871,955 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | Cl[C:2]1[N:3]=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=... | OB(O)c1ccccc1 | COc1ccc(Cl)nn1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 3-chloro-6-methoxy-pyridazine (4.0 g, 27.7 mmol) and phenyl boronic acid (5.1 g, 41.6 mmol) in toluene (160 mL) was degassed and tetrakis(triphenylphosphine)palladium (960 mg, 0.83 mmol) and 2M sodium carbonate (29.3 mL, 58.7 mmol) were added. The mixture was heated to reflux under nitrogen for 6 h, then c... | COc1ccc(-c2ccccc2)nn1 | null | 74 | null |
1,692,815 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:6]=2[CH:22]=1.[N+:23]([O-])([OH:25])=[O:24]>C(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([N+:23]([O-:25])=[O:24])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=3)... | O=[N+]([O-])O | CCOC(=O)c1c(-c2ccc(F)cc2)oc2ccc(Br)cc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 0 | 0.5 | To a solution of ethyl 5-bromo-2-(4-fluorophenyl)benzofuran-3-carboxylate (50 g, 137.6 mmol) in CHCl3 (500 mL), fuming HNO3 (50 mL) was added dropwise at −15° C. and the mixture was stirred for 0.5 hour. The reaction mixture was poured into ice water and extracted with CH2Cl2. The organic layer was washed with a.q. sat... | CCOC(=O)c1c(-c2ccc(F)cc2)oc2cc([N+](=O)[O-])c(Br)cc12 | null | 66 | null |
1,164,915 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:12][N:13]3[CH2:18][CH2:17][N:16]([C:19]([CH3:24])([CH3:23])[C:20]([NH2:22])=[O:21])[CH2:15][CH2:14]3)[N:8]2[CH3:11])=[C:4]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[N:3]=1.[CH:31]([C:34]1[NH:35][C:36]2[CH:42]=[CH:41][CH:40]=[CH:39][C:37]=2[N:38]=1)([CH3:33])[CH3:32]>>[C... | CC(C)c1nc2ccccc2[nH]1 | Cn1c(CN2CCN(C(C)(C)C(N)=O)CC2)nc2c(N3CCOCC3)nc(Cl)nc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2-(4-((2-Chloro-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperazin-1-yl)-2-methylpropanamide (75 mg) was reacted with 2-isopropylbenzimidazole via General Procedure I for Buchwald coupling to give 24.9 mg 439 following reverse phase purification. MS (Q1) 561.7 (M)+ | CC(C)c1nc2ccccc2n1-c1nc(N2CCOCC2)c2nc(CN3CCN(C(C)(C)C(N)=O)CC3)n(C)c2n1 | null | null | null |
826,119 | ord_dataset-0ca5627a13c049a99463095023b09fe5 | null | 2008-01-01T00:06:00 | true | [Br:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([O:18][CH2:19][CH3:20])([CH3:17])[CH3:16])[C:5]([NH2:21])=[CH:4][CH:3]=1.[F:22][C:23]([F:35])([F:34])[O:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[CH:27][CH:26]=1>>[Br:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11... | CCOC(C)(C)c1ccccc1Oc1nc(Br)ccc1N | O=C=Nc1ccc(OC(F)(F)F)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Example 582 was prepared from 6-bromo-2-(2-(2-ethoxypropan-2-yl)phenoxy)pyridin-3-amine and p-trifluoromethoxyphenyl isocyanate according to the procedure described for Example 2. (M−EtO)=508, 510. 1H NMR (400 MHz, DMSO-d6) δppm 0.82 (t, J=7.0 Hz, 3H), 1.53 (s, 6H), 3.21 (q, J=7.0 Hz, 2H), 7.21 (dd, J=8.1, 1.3 Hz, 1H),... | CCOC(C)(C)c1ccccc1Oc1nc(Br)ccc1NC(=O)Nc1ccc(OC(F)(F)F)cc1 | null | null | null |
1,314,160 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([P:15](=[O:22])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])([F:14])[F:13])[N:8]=[C:7](/[CH:23]=[N:24]/O)[CH:6]=[CH:5]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([P:15](=[O:22])([O:16][CH2:1... | CCOP(=O)(OCC)C(F)(F)c1cc2nc(/C=N/O)ccc2cc1Br | null | null | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)(Cl)Cl | CC#N | null | null | null | null | null | null | null | null | null | 100 | 1 | To a stirred solution of diethyl [(6-bromo-2-[(E)-(hydroxyimino)methyl]quinolin-7-yl)(difluoro)methyl]phosphonate (520 mg, 1.189 mmol) in acetonitrile (30 mL) at room temperature were added triphenylphosphine (1.248 g, 4.76 mmol) and carbon tetrachloride (230 μL, 2.383 mmol). The reaction mixture was stirred at 100° C.... | CCOP(=O)(OCC)C(F)(F)c1cc2nc(C#N)ccc2cc1Br | null | null | null |
1,508,579 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:15]1([NH:18][C:19](=[O:47])[C:20]2[CH:25]=[C:24]([N:26]3[CH:31]=[CH:30][N:29]=[C:28]([NH:32][C@@H:33]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C@@H:34]([CH3:37])[CH:35]=O)[C:27]3=[O:44])[C:23]([CH3:45])=[C:22]([F:46])[CH:21]=2)[CH2:17][CH2:16]1.[NH:48]1[CH2:52][CH2:51][CH... | Cc1c(F)cc(C(=O)NC2CC2)cc1-n1ccnc(N[C@@H](c2ccccc2)[C@@H](C)C=O)c1=O | C1CCNC1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 22 | 2 | Sodium triacetoxyborohydride (0.284 g) was added to N-cyclopropyl-3-fluoro-4-methyl-5-[3-{[(1R,2R)-2-methyl-3-oxo-1-phenylpropyl]amino}-2-oxopyrazin-1(2H)-yl]benzamide (Example 328e, 0.3 g), pyrrolidine (0.221 mL) and Hunig's Base (0.467 mL) in DCM (15 mL). The resulting suspension was stirred at 22° C. for 2 h. The re... | Cc1c(F)cc(C(=O)NC2CC2)cc1-n1ccnc(N[C@@H](c2ccccc2)[C@@H](C)CN2CCCC2)c1=O | null | null | null |
698,630 | ord_dataset-4e9c2fa02a7544fd839206719263345f | null | 2006-01-01T00:02:00 | true | [Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28]([N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[O:29])[N:27]=2)[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28]([N:30]3[CH2:31][CH2:32][CH2:33][CH2... | CC(C)(C)[Si](OC1CN(c2nc(C(=O)N3CCCCC3)cs2)C1)(c1ccccc1)c1ccccc1 | null | null | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of 3-t-butyldiphenylsilyloxy-1-(4-piperidinocarbonyl-1,3-thiazol-2-yl)azetidine (607 mg, 1.20 mmol) (obtained as described in Reference Example 27(1)) in anhydrous tetrahydrofuran (25 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (1.40 ml, 1.40 mmol) in an ice bath, an... | O=C(c1csc(N2CC(O)C2)n1)N1CCCCC1 | null | 96.6 | null |
1,707,807 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([O-:28])=[O:27])=[CH:22][CH:21]=1.[Na+]>>[CH3:8][C:7]1[O:6][C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[N:4][C:3]=... | COC(=O)c1ccc(-c2nc(CCl)c(C)o2)cc1 | Cc1ccc(S(=O)[O-])cc1 | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of chloride 2 (1.54 g, 5.8 mmol) and sodium 4-methylbenzenesulfinate (1.08 g, 6.1 mmol) gave benzoate 3 (1.96 g, 88%) as a white powder: mp (EtOAc) 177-178° C.; 1H NMR (CDCl3) δ 8.08 (ddd, J=8.7, 2.0, 1.6 Hz, 2H, H-2, H-6), 7.92 (ddd, J=8.7, 2.0, 1.6 Hz, 2H, H-3, H-5), 7.69 (ddd, J=8.3, 1.9, 1.7 Hz, 2H, H-2′,... | COC(=O)c1ccc(-c2nc(CS(=O)(=O)c3ccc(C)cc3)c(C)o2)cc1 | null | 87.7 | null |
1,505,842 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [I-].[C:2]([O:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][N+:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:11][C:10]=1[N+:22]([O-])=O)=[O:8])([CH3:5])([CH3:4])[CH3:3].[H][H]>CO>[NH2:22][C:10]1[CH:11]=[C:12]([CH:15]2[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]2)[CH:13]=[CH:14][C:9]=1[C:7]([O:6][C:2]([CH3:3])([C... | [H][H] | C[n+]1ccc(-c2ccc(C(=O)OC(C)(C)C)c([N+](=O)[O-])c2)cc1 | null | [I-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | 0.48 g of platine (IV) oxide (2.12 mmol) is added to a solution of 26.8 g of 4-(4-(tert-butoxycarbonyl)-3-nitrophenyl)-1-methylpyridinium iodide (60.6 mmol) in 200 mL of methanol placed in a reactor made in stainless steel. The reaction medium is brought under 5 bar of hydrogen for 24 h. The catalyst is filtered and th... | CN1CCC(c2ccc(C(=O)OC(C)(C)C)c(N)c2)CC1 | null | 140.9 | null |
648,366 | ord_dataset-5d77a731aa10488794c824ad12021f57 | null | 2004-01-01T00:09:00 | true | [N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9](=[S:12])[NH:10][NH2:11])[CH:2]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH:19]=O>C(O)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9](=[S:12])[NH:10][N:11]=[CH:19][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=2)[CH:2]=1 | O=Cc1ccccn1 | NNC(=S)NCc1cccnc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from a mixture of 4-(3-picolyl)-3-thiosemicarbazide (100 mg, 0.549 mmol), 2-pyridinecarboxaldehyde (52 μL, 0.549 mmol) and glacial acetic acid (62 μL) similar to Example 3 and isolated as a white solid (87 mg, 58%). 1H NMR (DMSO-d6): 11.76 (s, 1H), 9.18 (t, J=6.0 Hz, 1H), 8.45-8.43 (m, 2... | S=C(NCc1cccnc1)NN=Cc1ccccn1 | null | null | null |
516,133 | ord_dataset-a495451286334c5c9bbcbd48a00c1350 | null | 2001-01-01T00:09:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([CH3:13])[CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH:12]([CH3:13])[CH2:11][CH2:10][N:9]2[S:20]([C:17]2[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=2)(=... | CC1CCNC1c1ccc(F)cc1 | Cc1ccc(S(=O)(=O)Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound, off-white solid, m.p. 112° C. and MS: m/e=354.2 (M+) was prepared in accordance with the general method of example 1e from (2RS,3RS)-2-(4-fluoro-phenyl)-3-methyl-pyrrolidine and toluene-4-sulfonyl chloride. | Cc1ccc(S(=O)(=O)N2CCC(C)C2c2ccc(F)cc2)cc1 | null | null | null |
1,280,493 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:16][C@H:15]([C:17]3[O:21][NH:20][C:19](=[O:22])[CH:18]=3)[CH2:14][CH2:13][N:12]2C(OC)=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:16][C@H:15]([C:17]3[O:21][NH:20][C:19](=[O:22])[CH:18]=3)[CH2:14][CH2:13][NH:12]2)=[CH:7][C... | COC(=O)N1CC[C@@H](c2cc(=O)[nH]o2)C[C@@H]1c1ccc(S(C)(=O)=O)cc1 | null | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | 20 | Trans-methyl 2-(4-(methylsulfonyl)phenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (301 mg, 0.79 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 2 mL, 28.55 mmol) and stirred at room temperature for 20 h. The solvent was evaporated and the residue purified by preparative HPLC (Instrument:... | CS(=O)(=O)c1ccc([C@H]2C[C@H](c3cc(=O)[nH]o3)CCN2)cc1 | null | 46.7 | null |
1,380,392 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [CH2:1]([C:8]1[N:13]=[C:12]([CH2:14][OH:15])[CH:11]=[C:10]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH2:1]([C:8]1[N:13]=[C:12]([CH:14]=[O:15])[CH:11]=[C:10]([C:16]2[CH:17]=[CH:18][C:19]([CH3:22])=[CH:2... | Cc1ccc(-c2cc(CO)nc(Cc3ccccc3)n2)cc1 | null | null | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 0.5 | To a solution of the product from Step B (0.102 g, 0.35 mmol) in CH2Cl2 (2 mL) was added the Dess-Martin periodinane (0.228, 0.53 mmol). After 30 min, the mixture was diluted satd. aq. NaHCO3 and extracted with CH2Cl2 (2×). The combined organic layers were dried, concentrated, and filtered through a small plug of SiO2 ... | Cc1ccc(-c2cc(C=O)nc(Cc3ccccc3)n2)cc1 | null | 545 | null |
1,476,701 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[CH3:15][O:16][C:17]1[N:22]=[C:21]([CH:23]([C:25]2[CH:30]=[CH:29][C:28]([S:31][CH3:32])=[CH:27][CH:26]=2)O)[CH:20]=[CH:19][C:18]=1[CH3:33].C(=O)(O)[O-].[Na+]>>[CH3:15][O:16][C:17]1[C:18]([CH3:33])=[CH:19][CH:20]=[C:21]([CH2:23][C:25]2[CH:26]=[CH:27][C:28]([S:31][CH3:32])=[CH:29][CH:30]=2)... | COc1nc(C(O)c2ccc(SC)cc2)ccc1C | null | null | CC[SiH](CC)CC | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 60 | 4 | Triethylsilane (5 mL) and trifluoroacetic acid (5 mL) were sequentially added to (6-methoxy-5-methylpyridin-2-yl)[4-(methylsulfanyl)phenyl]methanol obtained in Reference Example 1-36(2) (2.13 g), and the mixture was stirred at 60° C. for four hours. The reaction solution was poured into saturated aqueous sodium bicarbo... | COc1nc(Cc2ccc(SC)cc2)ccc1C | null | null | null |
1,348,724 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [Cl:1][C:2]1[C:3]([NH:12][C:13]2[C:18]([Cl:19])=[CH:17][N:16]=[C:15](Cl)[N:14]=2)=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:7][CH3:8])=[O:6].[NH2:21][C:22]1[CH:34]=[CH:33][C:25]2[N:26]([CH3:32])[C:27](=[O:31])[CH2:28][CH2:29][CH2:30][C:24]=2[CH:23]=1.Cl>CC(O)C.O1CCOCC1>[Cl:1][C:2]1[C:3]([NH:12][C:13]2[C:18]([Cl:19])=[CH:... | CN1C(=O)CCCc2cc(N)ccc21 | CNC(=O)c1cccc(Cl)c1Nc1nc(Cl)ncc1Cl | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | 3-Chloro-2-(2,5-dichloro-pyrimidin-4-ylamino)-N-methyl-benzamide (36.0 mg, 0.109 mmol) and 7-amino-1-methyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (22.8 mg, 0.120 mmol) were slurried in iPrOH (1.5 mL) prior to adding ˜0.2 mL of 4N HCl in dioxane. This mixture was heated in a microwave reactor (sealed vessel) at 120° C... | CNC(=O)c1cccc(Cl)c1Nc1nc(Nc2ccc3c(c2)CCCC(=O)N3C)ncc1Cl | null | 70.1 | null |
869,730 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | [F:1][C:2]1([F:30])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:29])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:8]([O:10][CH2:11][CH2:12][CH2:13][N:14](CC2C=CC=CC=2)[CH3:15])=[O:9])[CH2:3]1>CO.[OH-].[Pd+2].[OH-].[C].[H][H]>[F:1][C:2]1([F:30])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:29])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:... | CN(CCCOC(=O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1)Cc1ccccc1 | [H][H] | null | [Pd+2] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of 41 mg of 3-(benzyl(methyl)amino)propyl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate in 2 ml of methanol, 10 mg of palladium hydroxide-carbon catalyst was added, followed by 2 hours' stirring at ambient temperature and pressure in hydrogen atmosphere. The reaction liquid was filtere... | CNCCCOC(=O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 | null | 99.5 | null |
1,231,962 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | O=[C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][CH2:4][C:5]#[N:6].[F:13][C:14]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:15]=1[C:16](=[S:19])[NH:17][NH2:18]>C(O)C>[F:13][C:14]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:15]=1[C:16]1[S:19][C:2]([CH2:3][CH2:4][C:5]#[N:6])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2... | N#CCCC(=O)c1ccccc1 | NNC(=S)c1cc(F)ccc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 90 | 16 | To a solution of 4-oxo-4-phenylbutanenitrile (0.076 g, 0.48 mmol) in ethanol (5 mL) was added 2,5-difluorobenzothiohydrazide (0.09 g, 0.48 mmol). After stirring at 90° C. for 16 hours, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with water and brin... | N#CCCC1(c2ccccc2)NN=C(c2cc(F)ccc2F)S1 | null | 55 | null |
486,640 | ord_dataset-7b02d32cc502407f94aea8e5caf405a2 | null | 2000-01-01T00:12:00 | true | [CH2:1]=[C:2]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[CH:15]1[C:27]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[CH:18]=[CH:17][CH:16]=1.CC[O-].[Na+]>CS(C)=O>[CH:13]1[C:14]2[CH:2]([CH2:1][CH:26]3[C:27]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:20]4[C:25]... | C=C1c2ccccc2-c2ccccc21 | c1ccc2c(c1)Cc1ccccc1-2 | null | CC[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 90 | null | A mixture of dibenzofulvene (1 g, 5.68 mmol), fluorene (0.93 g, 5.68 mmol) and EtONa (0.19 g, 2.79 mmol) in DMSO (20 mL) was heated at 90° C. for 16 hours, and was then cooled to room temperature. After carrying out the work-up, as reported in Example 8, 0.55 g of bis(9-fluorenyl)methane were obtained, with a yield of ... | c1ccc2c(c1)-c1ccccc1C2CC1c2ccccc2-c2ccccc21 | null | 28.1 | null |
186,758 | ord_dataset-3ec273742a0345ea916ad5fd071167f2 | null | 1989-01-01T00:04:00 | true | [C:1](=[O:13])([O:11][CH3:12])[O:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[Br:10].[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O>[C:1](=[O:13])([O:11][CH3:12])[O:2][C:3]1[CH:8]=[C:7]([N+:14]([O-:16])=[O:15])[C:6]([F:9])=[CH:5][C:4]=1[Br:10] | O=[N+]([O-])O | COC(=O)Oc1ccc(F)cc1Br | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | 2 | A rapidly stirred solution of 946 g (3.8 moles) of 2-bromo-4-fluorophenyl methyl carbonate in 1292 mL of sulfuric acid was cooled to 5°-10° C., and 368 g (4.18 moles) of 70% nitric acid was added dropwise over two hours. Upon complete addition, the reaction mixture was allowed to warm to ambient temperature and was sti... | COC(=O)Oc1cc([N+](=O)[O-])c(F)cc1Br | null | 92.3 | null |
1,387,724 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([Cl:9])[CH:3]=1.[Br:10][CH2:11][C:12](Br)=[O:13].C(N(CC)CC)C>C(Cl)Cl>[Br:10][CH2:11][C:12]([NH:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([Cl:9])[CH:3]=1)=[O:13] | O=C(Br)CBr | Nc1cc(Cl)nc(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 0 | 0.08 | To a stirring solution of 4-amino-2,6-dichloro-pyridine (4.7 g, 28.8 mmol) in DCM, bromoacetyl bromide (2.56 ml, 29.4 mmol) is added. The solution is cooled to 0° C. and stirred for 5 minutes before treating dropwise with triethylamine (7.87 ml, 57.7 mmol). The reaction mixture is gradually allowed to warm to RT and st... | O=C(CBr)Nc1cc(Cl)nc(Cl)c1 | null | null | null |
1,175,633 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | [NH2:1][C:2](=O)[C@@H:3]([NH:27][C:28]([C:30]1([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)=[O:29])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)(=[O:19])=[O:18])=[CH:13][CH:12]=2)=... | CN1CCN(S(=O)(=O)c2ccc(-c3ccc(C[C@H](NC(=O)C4(NC(=O)OC(C)(C)C)CCOCC4)C(N)=O)cc3)cc2)CC1 | null | null | CC[N+](CC)(CC)S(=O)(=O)N=C([O-])OC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 18 | (S)-tert-Butyl 4-(1-amino-3-(4′-(4-methylpiperazin-1-ylsulfonyl)biphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 29, step (i), 267 mg) in dichloromethane (10 mL) was treated with Burgess' reagent (202 mg) and the mixture was stirred at room temperature for 18 h. The solvent was partia... | CN1CCN(S(=O)(=O)c2ccc(-c3ccc(C[C@@H](C#N)NC(=O)C4(NC(=O)OC(C)(C)C)CCOCC4)cc3)cc2)CC1 | null | 96.4 | null |
998,892 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH2:11])=[S:10].Br[CH:13]([CH2:17][CH3:18])[C:14](O)=[O:15]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[S:10][CH:13]([CH2:17][CH3:18])[C:14](=[O:15])[N:11]=1 | CCC(Br)C(=O)O | NC(=S)Nc1ccccc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Synthesis was performed from N-(2-chlorophenyl)thiourea and 2-bromo-butyric acid according to Method C1. | CCC1SC(Nc2ccccc2Cl)=NC1=O | null | null | null |
1,260,275 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:30]([F:33])([F:32])[F:31])[O:13][N:12]=[C:11]([C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]([C:24]#[C:25][Si](C)(C)C)=[CH:16][CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Cl-].[NH4+].C(OCC)(=O)C>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]... | C[Si](C)(C)C#Cc1ccc(C2=NOC(c3cc(Cl)cc(Cl)c3)(C(F)(F)F)C2)c2ccccc12 | null | null | CCCC[N+](CCCC)(CCCC)CCCC | [Cl-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | A solution of tetrabutylammonium chloride (1 M in THF, 2.25 ml) is slowly added to a solution of crude 5-(3,5-dichloro-phenyl)-5-trifluoromethyl-3-(4-trimethylsilanylethynyl-naphthalen-1-yl)-4,5-dihydro-isoxazole (step A) in THF (25 ml) at 5° C. After 3 hours at 5° C. a saturated solution of ammonium chloride and ethyl... | C#Cc1ccc(C2=NOC(c3cc(Cl)cc(Cl)c3)(C(F)(F)F)C2)c2ccccc12 | null | null | null |
209,837 | ord_dataset-e0a818f9350b46cdb184d2ac404ede9f | null | 1990-01-01T00:06:00 | true | [Na].[F:2][C:3]1[CH:4]=[C:5]([N:9]2[CH:13]=[N:12][C:11]([OH:14])=[N:10]2)[CH:6]=[CH:7][CH:8]=1.Br[CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(O)C.CS(C)=O>[CH2:20]([O:19][C:17]([CH:16]([O:14][C:11]1[N:12]=[CH:13][N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([F:2])[CH:4]=2)[N:10]=1)[CH3:22])=[O:18])[CH3:21] | CCOC(=O)C(C)Br | Oc1ncn(-c2cccc(F)c2)n1 | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CS(C)=O | null | null | null | null | null | null | null | null | null | 0 | 2 | A 1.7 g portion of sodium was dissolved in 50 ml of absolute ethanol, and that solution was added to a solution of 13.3 g of 1-(3-fluorophenyl)-3-hydroxy-1,2,4-1H-triazole in 150 ml of dimethylsulfoxide. The solution was heated on the steam bath for 15 minutes, and then 13.5 g of ethyl 2-bromopropionate was added and t... | CCOC(=O)C(C)Oc1ncn(-c2cccc(F)c2)n1 | null | 32.3 | null |
522,987 | ord_dataset-262b40ea420c471da9b9244fe9b8f645 | null | 2001-01-01T00:10:00 | true | [ClH:1].O.[NH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[Al+3].[Cl-].[Cl-].[Cl-].O.[CH:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[ClH:1].[C:15]1([C:6]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:7][CH2:8][NH:3][CH2:4][CH2:5]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1 | O=C1CCNCC1 | c1ccccc1 | null | Cl | [Al+3] | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of 4-piperidone monohydrate hydrochloride (15.0 g, 97.6 mmol, 1.00 equiv) and AlCl3 (130 g, 976 mmol, 10.0 equiv) in anhydrous benzene (600 mL) was stirred at reflux for 4 hours. The mixture was cooled to room temperature, poured into ice (300 g) and water (50 mL), and filtered. The solid was washed with tolu... | c1ccc(C2(c3ccccc3)CCNCC2)cc1 | null | 72 | null |
1,168,154 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | F[C:2]1[CH:28]=[CH:27][C:5]2[N:6]=[C:7]([C:9]3[C:10]([NH2:26])=[N:11][CH:12]=[C:13]([C:15]4[CH:16]=[N:17][N:18]([CH:20]5[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]5)[CH:19]=4)[CH:14]=3)[S:8][C:4]=2[CH:3]=1.[Cl:29]C1SC2C=C(Cl)C=CC=2N=1>>[Cl:29][C:2]1[CH:28]=[CH:27][C:5]2[N:6]=[C:7]([C:9]3[C:10]([NH2:26])=[N:11][CH:12]=[C:13... | Nc1ncc(-c2cnn(C3CCNCC3)c2)cc1-c1nc2ccc(F)cc2s1 | Clc1ccc2nc(Cl)sc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Same procedure as 3-(6-fluorobenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine except using 2,6-dichloro-1,3-benzothiazole in place of 2-chloro-6-fluorobenzothiazole to afford the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=2.10-2.30 (m, 4H), 3.06-3.18 (m, 2H), 3.41 (d, J=13.2... | Nc1ncc(-c2cnn(C3CCNCC3)c2)cc1-c1nc2ccc(Cl)cc2s1 | null | null | null |
1,474,966 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [CH3:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[CH:15]1([NH2:18])[CH2:17][CH2:16]1>>[CH:15]1([NH:18][CH:11]2[CH2:12][CH2:13][N:8]([C:5]3[N:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=3)[CH2:9][CH2:10]2)[CH2:17][CH2:16]1 | NC1CC1 | Cc1cnc(N2CCC(=O)CC2)nc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound is prepared from 1-(5-methyl-pyrimidin-2-yl)-piperidin-4-one and cyclopropylamine following a procedure analogous to that described in Intermediate 7. LC (method 1): tR=0.55 min; Mass spectrum (ESI+): m/z=233 [M+H]+. | Cc1cnc(N2CCC(NC3CC3)CC2)nc1 | null | null | null |
459,031 | ord_dataset-aa5bc55d09b7465ab353e144a7ac3ad1 | null | 2000-01-01T00:03:00 | true | Cl[Si:2]([CH3:18])([CH3:17])[CH:3]1[C:14]2[C:6](=[CH:7][C:8]3[CH2:9][CH2:10][CH2:11][C:12]=3[CH:13]=2)[C:5]([CH3:15])=[C:4]1[CH3:16].CCN(CC)CC.[C:26]([NH2:30])([CH3:29])([CH3:28])[CH3:27]>CCCCCC>[CH3:27][C:26]([NH:30][Si:2]([CH3:18])([CH3:17])[CH:3]1[C:14]2[C:6](=[CH:7][C:8]3[CH2:9][CH2:10][CH2:11][C:12]=3[CH:13]=2)[C:... | CC1=C(C)C([Si](C)(C)Cl)c2cc3c(cc21)CCC3 | CC(C)(C)N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CCCCCC | null | null | null | null | null | null | null | null | null | null | 16 | Chlorodimethyl(1,5,6,7-tetrahydro-2,3-dimethyl-s-indacen-1-yl) silane (3.537 g, 0.01217 moles) was stirred in hexane (50 mL) as NEt3 (1.94 g, 0.01916 moles) and t-butylamine (1.12 g, 0.01533 moles) were added. This mixture was allowed to stir 16 hours. After the reaction period the mixture was filtered and the volatile... | CC1=C(C)C([Si](C)(C)NC(C)(C)C)c2cc3c(cc21)CCC3 | null | 92.7 | null |
1,660,856 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.COCCOC.Br[C:15]1[CH:16]=[N:17][C:18]([N:21]2[CH2:26][CH2:25][CH:24]([C:27]3[C:36]([CH:37]([F:48])[C:38]4[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=4)=[C:35]([CH:49]4[CH2:54][CH2:53][C:52]([F:56])([F:55])[CH2:51][CH2:50]4)[C:34]4[CH:33]([O:57]CC5C=... | OC1CCNCC1 | COc1ccc(COC2CC(C)(C)Cc3nc(C4CCN(c5ncc(Br)cn5)CC4)c(C(F)c4ccc(C(F)(F)F)cc4)c(C4CCC(F)(F)CC4)c32)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | Reactions similar to those of Reference Example 13 and Example 7 were performed except for using 4-hydroxy piperidine and 1,2-dimethoxyethane instead of isonipecotic acid ethyl ester and toluene, and from 150 mg (0.180 mmol) of (−)-2-[1-(5-Bromopyrimidin-2-yl)piperidin-4-yl]-4-(4,4-difluorocyclohexyl)-3-{fluoro[4-(trif... | CC1(C)Cc2nc(C3CCN(c4ncc(N5CCC(O)CC5)cn4)CC3)c(C(F)c3ccc(C(F)(F)F)cc3)c(C3CCC(F)(F)CC3)c2C(O)C1 | null | null | null |
142,293 | ord_dataset-84dc0c9e5fb4424687194ef8d14d1c22 | null | 1986-01-01T00:04:00 | true | [F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[C:5]([NH2:10])[CH:4]=1.[CH3:13][O:14][C:15]1[CH:23]=[C:22]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:21]=[CH:20][C:16]=1[C:17](O)=O>>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:8]=[CH:7][C:6]2[N:9]=[C:17]([C:16]3[CH:20]=[CH:21][C:22]([NH:24][S:25]([CH3:28])(=[O:27]... | COc1cc(NS(C)(=O)=O)ccc1C(=O)O | Nc1ccc(C(F)(F)F)cc1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared analogously to Example 14 from 4-trifluoromethyl-1,2-phenylenediamine and 2-methoxy-4-methanesulfonylamino-benzoic acid. | COc1cc(NS(C)(=O)=O)ccc1-c1nc2ccc(C(F)(F)F)cc2[nH]1 | null | null | null |
83,843 | ord_dataset-7bed824f566d4af0b51d74d386b14bd6 | null | 1981-01-01T00:07:00 | true | [CH3:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:14]=[CH:15][CH:16]=2)[C:7]=1[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.[Br:17]N1C(=O)CCC1=O>ClCCl>[Br:17][C:16]1[CH:15]=[N:14][N:6]2[C:7]([C:8]3[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=3)=[C:2]([CH3:1])[CH:3]=[N:4][C:5]=12 | Cc1cnc2ccnn2c1-c1cccnc1 | O=C1CCC(=O)N1Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 0 | null | A mixture of 1.65 g. of 6-methyl-7-(3-pyridyl)pyrazolo[1,5-a]pyrimidine and 1.54 g. of N-bromosuccinimide in 50 ml. of dichloromethane is heated on a steam bath for 15 minutes. The mixture is poured into 100 ml. of ice cold 2.5 N sodium hydroxide. The dichloromethane layer is separated, dried over anhydrous sodium sulf... | Cc1cnc2c(Br)cnn2c1-c1cccnc1 | null | null | null |
528,044 | ord_dataset-f027aa93238e424fbbf9bad1c7699adc | null | 2001-01-01T00:12:00 | true | O.O.[Sn](Cl)Cl.[CH2:6]([S:8]([C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1)(=[O:10])=[O:9])[CH3:7].[OH-].[Na+]>C(O)C>[CH2:6]([S:8]([C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)(=[O:10])=[O:9])[CH3:7] | CCS(=O)(=O)c1ccc([N+](=O)[O-])cc1 | null | null | Cl[Sn]Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | 25 | null | Tin (II) chloride dihydrate (51.89 g, 0.230 mol) was added to 1-(ethylsulfonyl)-4-nitrobenzene (10 g, 0.046 mol) in ethanol (250 ml) then heated under reflux for 16 h. The mixture was cooled to room temperature and treated with aqueous sodium hydroxide (2N, 100 ml). The product was then extracted into ethyl acetate (3×... | CCS(=O)(=O)c1ccc(N)cc1 | null | null | null |
1,481,989 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10](=[O:35])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:22]=[C:21]([C:23]([NH:25][CH:26]([CH:31]([CH3:33])[CH3:32])[C:27]([O:29]C)=[O:28])=[O:24])[O:20][N:19]=2)=[CH:14][C:13]=1[CH3:34].[Li+].[OH-].Cl>C1COCC1.O>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3... | COC(=O)C(NC(=O)c1cc(-c2ccc(NC(=O)Nc3c(F)cccc3F)c(C)c2)no1)C(C)C | null | null | Cl | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 25 | 0.25 | A mixture of the crude compound of step 8, LiOH (3.0 equiv.) and 50 ml of 5:1 THF/water was stirred at room temperature for 15 minutes. The reaction mixture was slightly acidified to pH <7 by adding 2N HCl and then evaporated to dryness under vacuum. The residue was dissolved in a chloroform and methanol mixture, adsor... | Cc1cc(-c2cc(C(=O)NC(C(=O)O)C(C)C)on2)ccc1NC(=O)Nc1c(F)cccc1F | null | null | null |
415,423 | ord_dataset-1cb9d78632144c5f8acfc3e9ff388678 | null | 1998-01-01T00:11:00 | true | [ClH:1].[CH2:2]([N:5](C(OC(C)(C)C)=O)[CH2:6][CH2:7][CH2:8][N:9](C(OC(C)(C)C)=O)[CH2:10][CH2:11][CH2:12][N:13]([CH2:21][CH2:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][NH:24]1)C(OC(C)(C)C)=O)[CH2:3][CH3:4]>CO>[ClH:1].[ClH:1].[ClH:1].[ClH:1].[CH2:2]([NH:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][CH2:11][CH2:12][NH:13][CH2:21]... | CCCN(CCCN(CCCN(CCC1CCCCN1)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 15 | 30 ml of 3N methanolic hydrochloric acid are added to a solution of 2.07 g (3.54 mmol) of 1-propyl-9-[2-(2-piperidyl)-ethyl]-1,5,9-tri-BOC-1,5,9-triazanonane in 5 ml of methanol, and the reaction mixture is stirred at room temperature for 15 hours. The crystallisate is filtered off and the filtration residue is suspend... | CCCNCCCNCCCNCCC1CCCCN1 | null | null | null |
602,037 | ord_dataset-82e842e611ef4a05b6e7f9ea0a46d52d | null | 2003-01-01T00:07:00 | true | CC1(C)[O:6][C@@H:5]([CH2:7][CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10]2)[CH2:4][O:3]1.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[N:9]1([CH2:8][CH2:7][C@H:5]([OH:6])[CH2:4][OH:3])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10]1 | CC1(C)OC[C@H](CCn2ccc3ccccc32)O1 | null | null | Cl | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 2.5 | To an ice cooled solution of 1-[2-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl]-1H-indole (520 mg, 2.12 mmol) in THF (10 ml) was added portionwise 1N-HCl (8.48 ml). After the addition was completed, the reaction mixture was stirred at room temperature for 2.5 hours. An aqueous solution of NaHCO3 was added, and the result... | OC[C@@H](O)CCn1ccc2ccccc21 | null | 103.3 | null |
1,663,127 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [O:1]=[C:2]1[NH:8][C:7]2[S:9][CH:10]=[CH:11][C:6]=2[C:5]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)=[N:4][CH2:3]1.[Br:22]Br>N1C=CC=CC=1>[Br:22][C:10]1[S:9][C:7]2[NH:8][C:2](=[O:1])[CH2:3][N:4]=[C:5]([C:12]3[CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=3)[C:6]=2[C... | BrBr | COC(=O)c1ccc(C2=NCC(=O)Nc3sccc32)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 0 | 1 | In a 20 mL dram screw-cap vial with septum was dissolved compound 493 (0.140 g, 0.466 mmol) in pyridine (3 mL) to give an orange solution. The mixture was cooled to 0° C. and bromine (0.029 mL, 0.559 mmol) was added dropwise. The reaction mixture was left to stir at 0° C. for 1 hour. The mixture was quenched with satur... | COC(=O)c1ccc(C2=NCC(=O)Nc3sc(Br)cc32)cc1 | null | 57.2 | null |
1,207,956 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12](=[O:24])[C:13]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=2[Cl:23])[CH2:7][CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC>C1COCC1>[Cl:23][C:14]1[CH:15]=[CH:16][C:17]([C:19]([F:20])([F:21])[F:22])=[CH:18][C:13]=1[C:12]([NH:11][C@H:8]1[CH2... | COC(=O)[C@H]1CC[C@H](NC(=O)c2cc(C(F)(F)F)ccc2Cl)CC1 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCOCC | null | null | null | null | null | null | null | null | null | 0 | 2 | To a solution of trans-4-(2-chloro-5-trifluoromethyl-benzoylamino)-cyclohexane carboxylic acid methyl ester (step 1)(95.2 g, 0.26 mol) in dry THF (1 L) under nitrogen at 0° C. is added lithium aluminum hydride pellets (20 g, 0.53 mol) portion wise over 3 hours. The reaction mixture is stirred at 0° C. for a further 2 h... | O=C(N[C@H]1CC[C@H](CO)CC1)c1cc(C(F)(F)F)ccc1Cl | null | null | null |
105,602 | ord_dataset-4ac1b977dc504cb5a6a8e85d7d777c45 | null | 1983-01-01T00:05:00 | true | C([N+](CCCC)(CCCC)CCCC)CCC.C(OC([NH:28][C@H:29]1[C@H:32]([CH3:33])[N:31]([S:34]([O-:37])(=[O:36])=[O:35])[C:30]1=[O:38])=O)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:28][C@H:29]1[C@H:32]([CH3:33])[N:31]([S:34]([OH:37])(=[O:35])=[O:36])[C:30]1=[O:38] | C[C@H]1[C@H](NC(=O)OCc2ccccc2)C(=O)N1S(=O)(=O)[O-] | null | null | [Pd] | CCCC[N+](CCCC)(CCCC)CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | (3S-trans)-3-[(Benzyloxycarbonyl)amino]-4-methyl-2-oxo-1-azetidinesulfonic acid tetra-n-butylammonium salt is dissolved in 250 ml of ethanol and 0.8 g of 5% palladium on charcoal is added. Hydrogen is bubbled through the stirred mixture for 90 minutes and the catalyst is filtered out. The addition of 12 ml of formic ac... | C[C@H]1[C@H](N)C(=O)N1S(=O)(=O)O | null | null | null |
1,421,139 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [CH2:1]([O:8][C:9]([NH:11][CH:12]([C:14]([OH:34])([PH2:32]=[O:33])[CH:15]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)[C:16](O)=[O:17])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:36][C@H:37]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=... | C[C@H](N)C(=O)OC(C)(C)C | CC(NC(=O)OCc1ccccc1)C(O)([PH2]=O)C(Cc1ccc(-c2ccccc2)cc1)C(=O)O | null | CN(C)C(On1nnc2ccccc21)=[N+](C)C | Cl | F[B-](F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 0.25 | The compound from step 1 (0.9 g) is solubilised in 10 ml of DMF in nitrogen, and t-butyl alaninate hydrochloride (450 mg), 2.5 ml of DIEA (6 eq) and 1.98 g of TBTU (3 eq) are successively added. The mixture is stirred for 15 min at ambient temperature and the reaction is processed as in step 4 of example 3. 1.10 g of e... | CC(NC(=O)C(Cc1ccc(-c2ccccc2)cc1)C(O)([PH2]=O)C(C)NC(=O)OCc1ccccc1)C(=O)OC(C)(C)C | null | 96.7 | null |
1,718,652 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.[OH:15][CH2:16][CH2:17][CH2:18][S:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1)(=[O:21])=[O:20]>>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:26](=[O:27])[C:25]2[CH:24]=[CH:23][C:22]([S:19]([CH2:18][CH2:1... | Nc1ccc(Cl)c(-c2ccccn2)c1 | O=C(O)c1ccc(S(=O)(=O)CCCO)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 5 g of 4-fluorobenzonitrile was used in Procedure Q with 3-mercapto-1-propanol to afford 4-(3-hydroxypropylthio)benzonitrile. 1.8 g of 4-(3-hydroxypropylthio)benzonitrile was reacted via Procedure T to give 4-(3-hydroxypropylthio)benzoic acid. 1.2 g of 4-(3-hydroxypropylthio)benzoic acid was reacted via Procedure R to ... | O=C(Nc1ccc(Cl)c(-c2ccccn2)c1)c1ccc(S(=O)(=O)CCCO)cc1 | null | null | null |
1,176,471 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | [O:1]=[C:2]1[CH:7]=[N:6][C:5]2[N:8]=[CH:9][CH:10]=[C:11]([O:12][C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:26])OC(C)(C)C)=[CH:15][CH:14]=3)[C:4]=2[NH:3]1.[C:27]([C:31]1[CH:35]=[C:34]([N:36]=C=O)[N:33]([C:39]2[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=2)[N:32]=1)([CH3:30])([CH3:29])[CH3:28]>>[C:27]([C:31]1[CH:35]... | Cc1ccc(-n2nc(C(C)(C)C)cc2N=C=O)cc1 | CC(C)(C)OC(=O)Nc1ccc(Oc2ccnc3ncc(=O)[nH]c23)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Method F1 was used with tert-butyl 4-(2-oxo-1,2-dihydropyrido[2,3-b]pyrazin-8-yloxy)phenylcarbamate and 3-tert-butyl-5-isocyanato-1-p-tolyl-1H-pyrazole to obtain the title compound (yield 64%). | Cc1ccc(-n2nc(C(C)(C)C)cc2NC(=O)Nc2ccc(Oc3ccnc4ncc(=O)[nH]c34)cc2)cc1 | null | 64 | null |
933,596 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [F:1][C:2]([F:35])([F:34])[CH2:3][S:4]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:25]C)=[CH:22][CH:23]=3)[CH:18]=[C:17]([CH3:27])[C:16]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:10][CH:9]=1)(=[O:6])=[O:5].B(Br)(Br)Br.CCOC(C)=O>C(Cl)Cl>[F:35][C:2]([F:1])([F:34])[CH2:3][S:4]... | COc1ccc2c(Oc3ccc(NS(=O)(=O)CC(F)(F)F)cc3)c(-c3ccccc3)c(C)cc2c1 | null | null | BrB(Br)Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 0 | 0.02 | To a stirring solution of 273 (0.14 g, 0.31 mmol) in CH2Cl2 (6 mL), chilled to −20° C. under N2, was added BBr3 (0.24 g, 0.94 mmol) dropwise, via syringe, over 1 minute. After 90 min at −20° C. the r×n was poured over 50 g ice followed by EtOAc (50 mL). The EtOAC layer was washed with brine (50 mL), dried (Na2SO4) and ... | Cc1cc2cc(O)ccc2c(Oc2ccc(NS(=O)(=O)CC(F)(F)F)cc2)c1-c1ccccc1 | null | null | null |
506,568 | ord_dataset-631d58dab387485c8eb0db4c20a232b7 | null | 2001-01-01T00:06:00 | true | Cl.[Br:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[OH-].[Na+].[N:13]1([N:19]2[C:28]3[C:23](=[CH:24][C:25]([CH2:29][N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)=[CH:26][CH:27]=3)[C:22](=[O:36])[C:21]([C:37](OCC)=[O:38])=[CH:20]2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>O>[Br:2][C:3]1[CH:10]=[CH:9][C:6](... | CCOC(=O)c1cn(N2CCOCC2)c2ccc(CN3CCOCC3)cc2c1=O | NCc1ccc(Br)cc1 | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 190 | null | 4-Bromobenzylamine hydrochloride (2.22 g) is suspended in water (5 mL) and neutralized with 2N aqueous NaOH (5 mL). The free amine is extracted with dichloromethane (2×25 mL). The organic layers are combined, washed with brine (5 mL), and dried with Na2SO4. The solution is concentrated in vacuo to afford 1.48 g of a cl... | O=C(NCc1ccc(Br)cc1)c1cn(N2CCOCC2)c2ccc(CN3CCOCC3)cc2c1=O | null | 68 | null |
223,345 | ord_dataset-59f453c3a3d34a89bfd97b6b8b151908 | null | 1991-01-01T00:02:00 | true | N[C:2]1[NH:6][CH2:5][N:4]([CH:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][C:8]2([CH3:17])[CH3:16])[C:3]=1[C:18](=[O:20])[CH3:19].N(OC(C)(C)C)=O>O1CCCC1>[CH3:16][C:8]1([CH3:17])[CH2:9][C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]1[N:4]1[C:3]([C:18](=[O:20])[CH3:19])=[CH:2][N:6]=[CH:5]1 | CC(=O)C1=C(N)NCN1C1c2ccccc2CC1(C)C | null | null | CC(C)(C)ON=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 1 | 13 Parts of [5-amino-3-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazol-4-yl]ethanone were dissolved in 167 parts of tetrahydrofuran. To the solution were added dropwise 7.7 parts of 2-methyl-2-propyl nitrite. After stirring at room temperature for 1 hour, the reaction mixture was evaporated to dryness. The residue... | CC(=O)c1cncn1C1c2ccccc2CC1(C)C | null | 51 | null |
497,542 | ord_dataset-18e9ed24dbd44e98b33bdc22aa7580a8 | null | 2001-01-01T00:04:00 | true | [C:1]1([S:7][CH2:8][C@@H:9]2[NH:12][C:11](=[O:13])[CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:14]OS([O-])=O.[K+]>CO>[C:1]1([S:7]([CH2:8][C@@H:9]2[NH:12][C:11](=[O:13])[CH2:10]2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 | O=S([O-])OO | O=C1C[C@H](CSc2ccccc2)N1 | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 24 | A solution of 4(R)-(phenylsulfanylmethyl)azetidin-2-one (from example 6, step A) (105 mg, 0.543 mmol) in MeOH (3 mL) was treated with an aqueous solution of oxone (167 mg, 0.272 mmol, 3 mL). After stirring at room temperature for 24 h, the reaction mixture was quenched with aqueous Na2S2O3 (10%, 1 mL) and concentrated.... | O=C1C[C@H](CS(=O)c2ccccc2)N1 | null | 157.4 | null |
1,398,667 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [Br:1][C:2]1[C:6]2[N:7]=[CH:8][NH:9][C:10](=O)[C:5]=2[NH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:14].C(=O)([O-])[O-].[K+].[K+]>>[Br:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([Cl:14])[C:5]=2[NH:4][CH:3]=1 | O=P(Cl)(Cl)Cl | O=c1[nH]cnc2c(Br)c[nH]c12 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 115 | 3 | A mixture of 7-bromo-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one (100 mg, 0.5 mmol) and 6 mL of POCl3 under argon was warmed at 115° C. After 3 hours, the mixture was cooled to room temperature and poured over 300 mL of ice, stirred, made basic with potassium carbonate and extracted with EtOAc. The combined organic layers... | Clc1ncnc2c(Br)c[nH]c12 | null | 93 | null |
833,604 | ord_dataset-ec576c604a9d47258c87c732a043ec71 | null | 2008-01-01T00:08:00 | true | [CH:1]1([CH2:7][CH2:8][C:9]([OH:11])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:12][C:13]1[C:22]([Cl:23])=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16][C:17]([N:24]1[CH2:29][CH2:28][CH:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH2:25]1)=[N:18]2>>[Cl:23][C:22]1[C:13]([NH:12][C:9](=[O:11])[CH2:8][CH2:7][CH:1]2[... | O=C(O)CCC1CCCCC1 | CCOC(=O)C1CCN(c2ccc3c(N)c(Cl)ccc3n2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared according to the method of example 62(a), using cyclohexanepropanoic acid (280 mg) and 1-(5-amino-6-chloro-2-quinolinyl)-4-piperidinecarboxylic acid, ethyl ester (Example 77(a)) (200 mg), to afford the sub-titled compound (240 mg). | CCOC(=O)C1CCN(c2ccc3c(NC(=O)CCC4CCCCC4)c(Cl)ccc3n2)CC1 | null | 84.9 | null |
821,210 | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | null | 2008-01-01T00:05:00 | true | Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]Br)=[CH:5][CH:4]=1.[P:11]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])[O:12]CC>>[C:6]1([CH2:9][P:11](=[O:12])([O:15][CH2:16][CH3:17])[O:18][CH2:19][CH3:20])[CH:7]=[CH:8][C:3]([CH2:2][P:11](=[O:12])([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])=[CH:4][CH:5]=1 | BrCc1ccc(CBr)cc1 | CCOP(OCC)OCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 130 | null | α, α′-Dibromo-p-xylene (5.28 g, 20 mmol, 1 equiv.) and triethyl phosphite (10.3 mL, 60 mmol, 3 equiv.) were placed in a flask with a magnetic stirring bar. A distillation apparatus was attached to collect ethyl bromide formed along with the reaction. The mixture was immersed in an oil bath and heated to 130° C. for 2 h... | CCOP(=O)(Cc1ccc(CP(=O)(OCC)OCC)cc1)OCC | null | 89.1 | null |
1,666,466 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | Cl[C:2]1[N:3]=[C:4]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[C:5]2[O:10][C:9]3[N:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:8]=3[C:6]=2[N:7]=1.[NH:22]1[C:30]2[CH:29]=[CH:28][CH:27]=[C:26](B(O)O)[C:25]=2[CH:24]=[CH:23]1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=... | OB(O)c1cccc2[nH]ccc12 | Cc1ccc2c(n1)oc1c(N3CCOCC3)nc(Cl)nc12 | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | 90 | null | To a solution of 2-chloro-7-methyl-4-morpholin-4-yl-pyrido[3′,2′:4,5]furo[3,2-d]pyrimidine, 18 (27 mg, 0.09 mmol, leg), indole-4-boronic acid (43 mg, 0.27 mmol, 3 eq) and PdCl2(PPh3)2 (12.4 mg, 0.02 mmol, 20 mol%) in a mixture of dioxane (2 mL) and H2O (1.0 mL) was added Na2CO3 (19 mg, 0.18 mmol, 2 eq) under Ar(g). The... | Cc1ccc2c(n1)oc1c(N3CCOCC3)nc(-c3cccc4[nH]ccc34)nc12 | null | 16 | null |
1,155,931 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][CH2:10][C:11]1[C:15]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:33]=[C:32]4[C:27]([CH:28]=[CH:29][CH:30]=[C:31]4[C:34]([O:36]C)=[O:35])=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)=[C:14]([CH:38]([CH3:40])[CH3:39])[O:13][N:12]=1.CO.[OH-].[Na+]>O1CCCC1>[Cl:1]... | COC(=O)c1cccc2ccc(-c3ccc(OCc4c(CCc5c(Cl)cccc5Cl)noc4C(C)C)cc3)cc12 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1CCOC1 | null | null | null | null | null | null | null | null | null | 100 | null | A solution of methyl 7-[4-({[3-[2-(2,6-dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-naphthalenecarboxylate (0.052 g, 0.09 mmol) in tetrahydrofuran (0.9 mL) was placed in a microwave reaction tube. Methanol (0.45 mL) was added followed by 1N sodium hydroxide (0.14 mL, 0.14 mmol). The tube wa... | CC(C)c1onc(CCc2c(Cl)cccc2Cl)c1COc1ccc(-c2ccc3cccc(C(=O)O)c3c2)cc1 | null | 77.3 | null |
1,267,596 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [C:1]12([C:11]3[CH:21]=[CH:20][C:14]([O:15][CH2:16][C:17](O)=[O:18])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:22][O:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH2:31].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:22][O:23][C... | COC(=O)c1ccccc1N | O=C(O)COc1ccc(C23CC4CC(CC(C4)C2)C3)cc1 | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 8 | To a mixture of [4-(1-adamantyl)phenoxy]acetic acid (85.9 mg, 0.30 mmol), 2-amino-benzoic acid methyl ester (0.07 mL, 0.54 mmol), N-(3-dimethylaminopropyl)-N′-ethyl carbodiimide HCl (EDC) (103.5 mg, 0.54 mmol) and 1-hydroxybenzotriazole (HOBt) (73.0 mg, 0.54 mmol) in DMF (3.6 mL) was added N,N-diisopropylethylamine, re... | COC(=O)c1ccccc1NC(=O)COc1ccc(C23CC4CC(CC(C4)C2)C3)cc1 | null | 36.9 | null |
1,222,387 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[N:11]=[C:10]2[S:12][C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])=[N:14][C:9]2=[CH:8][CH:7]=1.[CH3:24][N:25]1[C:29]([C:30](O)=[O:31])=[CH:28][N:27]=[CH:26]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH:18]1(... | Cn1cncc1C(=O)O | Nc1cccc(Oc2ccc3nc(NC(=O)C4CC4)sc3n2)c1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | In the same manner as in Example 101-4 and using N-[5-(3-aminophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (124 mg, 0.280 mmol), 1-methyl-1H-imidazole-5-carboxylic acid (71.9 mg, 0.570 mmol), HATU (260 mg, 0.684 mmol), N,N-diisopropylethylamine (298 μL, 1.71 mmol) and N,N-dimethylformamide (4 mL) as... | Cn1cncc1C(=O)Nc1cccc(Oc2ccc3nc(NC(=O)C4CC4)sc3n2)c1 | null | 88 | null |
83,409 | ord_dataset-7bed824f566d4af0b51d74d386b14bd6 | null | 1981-01-01T00:07:00 | true | Cl.CS[C:4]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)([CH3:8])[C:5]([OH:7])=[O:6]>[Zn].O>[S:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[CH:4]([CH3:8])[C:5]([OH:7])=[O:6] | CSC(C)(C(=O)O)c1cccs1 | null | null | Cl | [Zn] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | 0.67 | Zinc powder (150 mg), 2 ml of conc. hydrochloric acid and 1 ml of water were added to 542 mg of α-methylthio-α-(2-thienyl)propionic acid, and the mixture was stirred at the refluxing temperature for 40 minutes. After cooling, it was extracted three times with 10 ml of diethyl ether. The organic layer was washed twice w... | CC(C(=O)O)c1cccs1 | null | 58.5 | null |
1,194,044 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[N:14]=[C:15]3[C:21]4[CH:22]=[CH:23][C:24]([C:26](O)=[O:27])=[CH:25][C:20]=4[O:19][CH2:18][CH2:17][N:16]3[CH:29]=2)=[N:11][CH:10]=[N:9]1.[CH3:30][S:31]([CH2:34][CH2:35][NH2:36])(=[O:33])=[O:32]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C... | O=C(O)c1ccc2c(c1)OCCn1cc(-c3ncnn3-c3ccccc3Cl)nc1-2 | CS(=O)(=O)CCN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2-(1-(2-Chlorophenyl)-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxylic acid (40 mg, 0.1 mmol) was reacted with 2-(methylsulfonyl)ethanamine to provide 2-(1-(2-chlorophenyl)-1H-1,2,4-triazol-5-yl)-N-(2-(methylsulfonyl)ethyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxamide... | CS(=O)(=O)CCNC(=O)c1ccc2c(c1)OCCn1cc(-c3ncnn3-c3ccccc3Cl)nc1-2 | null | null | null |
235,250 | ord_dataset-1acb071a357f438ea5993287375971cf | null | 1991-01-01T00:10:00 | true | [CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]2[CH:16]=[C:15]([CH2:17][CH:18]=[CH2:19])[CH:14]=[CH:13][C:12]=2[O:20][CH2:21][CH2:22]Cl)[CH:5]=1)[CH:2]=[CH2:3].[I-].[Na+].[CH2:26]([NH:28][CH2:29][CH3:30])[CH3:27]>>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]2[CH:16]=[C:15]([CH2:17][CH:18]=[CH2:19])[CH:... | CCNCC | C=CCc1ccc(O)c(-c2cc(CC=C)ccc2OCCCl)c1 | null | [I-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A mixture was prepared by mixing 0.5 g of 4-allyl-2-[5allyl-2-(2-chloroethoxy)phenyl]phenol and 1.5 g of sodium iodide with 20 ml of acetonitryl. The mixture was refluxed by heating for 4 hours with stirring, 1 ml of diethylamine was added thereinto, refluxed for 3 hours with stirring and concentrated. The concentrate,... | C=CCc1ccc(O)c(-c2cc(CC=C)ccc2OCCN(CC)CC)c1 | null | null | null |
1,230,500 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [NH2:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[N:15]=[C:14]3[C:10]([N:11]=[CH:12][N:13]3[C@@H:16]3C[C@H](NC(=O)CO)[C@@H:18]([OH:26])[C@H:17]3[OH:27])=[C:9]([NH:28][CH2:29][CH:30]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)C3C=CC=CC=3)[N:8]=2)[CH:6]=1.ClC1N=C2C(N=CN2[C@@H]2C[C@H:56]([NH:58][C:59]([CH2:61][O:62]C(=O)C)=[O:60]... | CC(=O)OCC(=O)N[C@H]1C[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(Cl)nc32)[C@H](O)[C@@H]1O | Nc1cn(-c2nc(NCC(c3ccccc3)c3ccccc3)c3ncn([C@@H]4C[C@H](NC(=O)CO)[C@@H](O)[C@H]4O)c3n2)cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound is prepared analogously to N-{(1S,2R,3S,4R)-4-[2-(4-amino-imidazol-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-hydroxy-acetamide (Intermediate ZU), by substituting (2S,3S,4R,5R)-5-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-carboxy... | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(-n4cnc(N)c4)nc32)[C@H](O)[C@@H]1O | null | null | null |
1,389,642 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.F[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([O:12][C:14]2[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=2)[CH:5]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7... | O=Cc1ccc(F)cc1 | Oc1cc(Cl)cc(C(F)(F)F)c1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 130 | null | To a solution of 3-chloro-5-(trifluoromethyl)phenol (2 g, 10.18 mmol) and 4-fluorobenzaldehyde (1.201 ml, 11.19 mmol) in DMF (30 mL), was added K2CO3 (2.109 g, 15.26 mmol). The mixture was heated at 130° C. overnight. After cooling, the reaction mixture was diluted in water, extracted with EA. The organic phase was was... | O=Cc1ccc(Oc2cc(Cl)cc(C(F)(F)F)c2)cc1 | null | 107.9 | null |
103,020 | ord_dataset-bdb961f26fac426eaa2de8f54a284acf | null | 1983-01-01T00:02:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]([C:15]([O:17]CC)=[O:16])=[CH:7]2)([O-:3])=[O:2].[OH-].[Na+]>Cl>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]([C:15]([OH:17])=[O:16])=[CH:7]2)([O-:3])=[O:2] | CCOC(=O)c1cc2cc([N+](=O)[O-])ccc2[nH]c1=O | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 9.7 g (37 mmol) of the above ester and 200 ml of 1 N sodium hydroxide is heated on the steam bath for 11/4 hours. The resulting suspension is poured over ice and acidified with 250 ml of 1 N hydrochloric acid. The solid is collected by filtration and washed with water and ethanol to give 8.15 g of the titl... | O=C(O)c1cc2cc([N+](=O)[O-])ccc2[nH]c1=O | null | 94.1 | null |
523,928 | ord_dataset-293186f5c9b441cab57f03cd3a18ac26 | null | 2001-01-01T00:11:00 | true | [C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[C:11]([C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=O)=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].Cl>N1C=CC=CC=1>[C:11]([C:15]1[CH:16]=[CH:17][C:18]([C:19]2[O:9][C:1](=[O:10])[C:2]3[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=3[N:4]=2)=[CH:22][CH:23]=1)([CH3:14])(... | CC(C)(C)c1ccc(C(=O)Cl)cc1 | Nc1ccccc1C(=O)O | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | 12 | To a stirred solution of anthranilic acid (34.3 g, 250 mmol) in pyridine (400 mL) was added 4-tert-butylbenzoyl chloride (94 mL, 500 mL) dropwise via an addition funnel. After stirring for 12 h, the solution was poured onto a slurry of ice and 2 N aqueous hydrochloric acid (100 mL). The mixture was extracted with dichl... | CC(C)(C)c1ccc(-c2nc3ccccc3c(=O)o2)cc1 | null | 22 | null |
1,459,043 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:14]4[C:19]([CH3:20])=[CH:18][C:17]([Cl:21])=[CH:16][C:15]=4[Cl:22])[CH2:12][CH2:13][N:7]3[C:6]=2[C:5]([CH2:23][OH:24])=[CH:4][CH:3]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:23]=[O:24])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:14]3[C:19]([CH3:20])=[C... | Cc1cc(Cl)cc(Cl)c1N1CCn2c1nc1c(Cl)ccc(CO)c12 | null | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CS(C)=O | null | null | null | null | null | null | null | null | null | 25 | 24 | To a solution of [8-chloro-1-(2,4-dichloro-6-methylphenyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-5-yl]methanol (163 mg, 0.426 mmol) and triethylamine (0.48 mL, 3.44 mmol) in dimethylsulfoxide (5.0 mL) was added sulfur trioxide-pyridine complex (0.44 g, 2.76 mmol) at room temperature. The mixture was stirred at room... | Cc1cc(Cl)cc(Cl)c1N1CCn2c1nc1c(Cl)ccc(C=O)c12 | null | 86.9 | null |
1,387,847 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=3)[C:10]([CH3:11])=[C:6]2[N:5]=[C:4]([CH3:19])[C:3]=1[CH:20]([OH:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]... | CCOC(=O)C(O)c1c(C)nc2c(C)c(-c3cccc(Cl)c3)nn2c1Cl | null | null | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | ClCCl | null | null | null | null | null | null | null | null | null | null | 1 | To a solution of ethyl 2-(7-chloro-2-(3-chlorophenyl)-3,5-dimethylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate (5.4 g, 12.33 mmol) in CH2Cl2 (100 ml) was added Dess-Martin periodinane (5.75 g, 13.56 mmol). The reaction was stirred 1 hr, then diluted with EtOAc (600 mL) and washed with saturated aqueous NaHCO3 (200 m... | CCOC(=O)C(=O)c1c(C)nc2c(C)c(-c3cccc(Cl)c3)nn2c1Cl | null | 72.3 | null |
713,595 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[C:4]1[C:15]([OH:17])=[O:16].[CH2:18](Br)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>CN(C=O)C>[CH2:18]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[C:4]1[C:15]([OH:17])=[O:16])[CH2:... | O=C(O)c1ccc2[nH]c(C(=O)O)cc2c1 | CCCCCCCCBr | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | null | Sodium hydride (60% suspension, 125 mg, 5 mmol) was added to a stirred solution of 1H-indole-2,5-dicarboxylic acid (525 mg, 2 mmol) in dry DMF (10 mL) and maintained at ambient temperature for 1 hour. The reaction was cooled to 0° C. and then octyl bromide (1.5 mL, 13 mmol) was added. After 3 days the reaction was quen... | CCCCCCCCn1c(C(=O)O)cc2cc(C(=O)O)ccc21 | null | 72.5 | null |
1,464,031 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [Br:1][C:2]1[N:3]=[C:4]([C:20]#[C:21][CH3:22])[S:5][C:6]=1[C:7]1[N:11]=[CH:10][N:9]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[N:8]=1.[I-].[NH2:24][N+:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>>[Br:1][C:2]1[N:3]=[C:4]([C:20]2[C:21]([CH3:22])=[N:24][N:25]3[CH:... | CC#Cc1nc(Br)c(-c2ncn(COCC[Si](C)(C)C)n2)s1 | N[n+]1ccccc1 | null | O=C([O-])[O-] | [I-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 29 | A mixture of 3-(4-bromo-2-prop-1-yn-1-yl-1,3-thiazol-5-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazole (0.514 g, 1.29 mmol), 1-aminopyridinium iodide (0.343 g, 1.54 mmol) and potassium carbonate (0.231 g, 1.67 mmol) in N,N-dimethylformamide (8.0 mL, 1.0E2 mmol) was stirred at rt for 29 hours. The mixture was... | Cc1nn2ccccc2c1-c1nc(Br)c(-c2ncn(COCC[Si](C)(C)C)n2)s1 | null | 64.8 | null |
1,344,859 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=1)[CH2:6][C:5]2([CH3:22])[CH3:21]>[Fe].C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=1)[CH2:6][C:5]2([CH3:22])[CH3:21] | CC1(C)CC(c2cccc([N+](=O)[O-])c2)Nc2ccc(Cl)cc21 | null | null | [Fe] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | null | null | Iron powder (43.0 g, 762 mmol), ethanol/water (3:1, 720 ml) and 6-chloro-4,4-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline (24.1 g, 76 mmol) were heated to reflux for 2 h. iron powder was filtered and the solvent was removed to afford 3-(6-chloro-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine as ... | CC1(C)CC(c2cccc(N)c2)Nc2ccc(Cl)cc21 | null | 95.9 | null |
123,298 | ord_dataset-a9b95e50436441ff8f3f12dd60d1e1b2 | null | 1984-01-01T00:10:00 | true | [S:1]([Cl:3])Cl.[CH3:4][NH:5][C:6](=[O:20])[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C(N(CC)CC)C>C(Cl)Cl>[Cl:3][S:1][N:5]([CH3:4])[C:6](=[O:20])[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19] | CCCCCCCCCCCCOC(=O)NC | ClSCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 5 | 2.3 | To a solution of 62 g (0.6 mole) of sulfur dichloride in 200 ml of methylene chloride cooled to 0° C. under a nitrogen atmosphere was added a solution made up of 97.4 g (0.4 mole) of n-dodecyl N-methylcarbamate, 44.5 g (0.44 mole) of triethylamine and 150 ml of methylene chloride. The addition took 2.3 hr while the tem... | CCCCCCCCCCCCOC(=O)N(C)SCl | null | 101.3 | null |
537,198 | ord_dataset-1884c7bf3d544afdb8d17b5d41b90a27 | null | 2002-01-01T00:03:00 | true | [C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH3:12])[C:6]=1[CH3:13])(=[O:3])[CH3:2].Cl[CH2:15][CH:16]1[CH2:18][O:17]1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:15][CH:16]2[O:17][CH2:18]2)=[C:7]([CH3:12])[C:6]=1[CH3:13])(=[O:3])[CH3:2] | ClCC1CO1 | CC(=O)Oc1ccc(O)c(C)c1C | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | Using 4.30 g of 4-acetoxy-2,3-dimethylphenol, 4.6 ml of chloromethyloxirane, 3.30 g of anhydrous potassium carbonate and 100 ml of methyl ethyl ketone, reaction and workup carried out as in Example 1-A gave about 6.05 g of 1-(4-acetoxy-2,3-dimethylphenoxy)-2,3-epoxypropane as brown oil. Using the epoxy compound thus ob... | CC(=O)Oc1ccc(OCC2CO2)c(C)c1C | null | null | null |
1,008,381 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[CH:10][C:9]=1[NH:19][C:20]([C:22]1[CH:23]=[N:24][C:25](Cl)=[CH:26][CH:27]=1)=[O:21])(C)(C)C.CCN(CC)CC.[CH2:37]1[C:40]2([CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[CH2:39][N:38]1C(OC(C)(C)C)=O>CS(C)=O>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14... | CC(C)(C)OC(=O)Nc1ccc(-c2cccs2)cc1NC(=O)c1ccc(Cl)nc1 | CC(C)(C)OC(=O)N1CC2(CCNCC2)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 90 | 18 | tert-Butyl[2-{[(6-chloropyridin-3-yl)carbonyl]amino}-4-(2-thienyl)phenyl]carbamate F (20 mg, 0.088 mmol) was dissolved in 1 mL of DMSO and treated with Et3N(0.010 mL) and tert-butyl 2,7-diazaspiro[3.5]nonane-2-carboxylate (20 mg, 0.047 mmol). The mixture was stirred at 90° C. for 18 h, partitioned between EtOAc and sat... | Nc1ccc(-c2cccs2)cc1NC(=O)c1ccc(N2CCC3(CC2)CNC3)nc1 | null | null | null |
387,882 | ord_dataset-44d518e567bd4c039d77233023f78bb2 | null | 1998-01-01T00:01:00 | true | [Cl:1][C:2]1[C:7]([NH:8][C:9]([C:11]2[C:12]([NH:17][CH2:18][CH3:19])=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])=[CH:6][CH:5]=[C:4]([Cl:20])[N:3]=1.C([O-])(=O)C.[K+].[Br:26]Br>C(O)(=O)C.O>[Cl:1][C:2]1[C:7]([NH:8][C:9]([C:11]2[C:12]([NH:17][CH2:18][CH3:19])=[N:13][CH:14]=[C:15]([Br:26])[CH:16]=2)=[O:10])=[CH:6][CH:5]=[C:4](... | CCNc1ncccc1C(=O)Nc1ccc(Cl)nc1Cl | BrBr | null | CC(=O)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 0.25 | To a solution of N-(2,6-dichloro-3-pyridinyl)-2-ethylamino-3-pyridinecarboxamide (7.4 g, 24 mmol) and potassium acetate (2.8 g, 28 mmol) in 90 mL of acetic acid was added bromine (1.2 mL, 23 mmol). After 15 min, the reaction mixture was diluted with water and the precipitate was collected by suction filtration to give ... | CCNc1ncc(Br)cc1C(=O)Nc1ccc(Cl)nc1Cl | null | 91.4 | null |
168,066 | ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | null | 1988-01-01T00:02:00 | true | Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][CH2:13][NH:14][CH:15]([CH3:17])[CH3:16])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[OH-:18].[Na+]>CS(C)=O>[ClH:2].[OH:18][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][CH2:13][NH:14][CH:15]([CH3:17])[CH3:16])(=[O:11])=[O:10])=[CH:5][CH:4]=1 | [OH-] | CC(C)NCCS(=O)(=O)c1ccc(Cl)cc1 | null | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | A solution of N-[2-[(4-chlorophenyl)sulfonyl]ethyl]-1-methylethanamine hydrochloride and sodium hydroxide in 500 ml of dimethyl sulfoxide is heated at 95° C. for 2 hrs with stirring. The solvent is removed by rotary evaporation (vacuum pump) and the residue is partitioned between water (pH adjusted to 7 by the addition... | CC(C)NCCS(=O)(=O)c1ccc(O)cc1 | null | null | null |
900,495 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [OH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][C:9]=2[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:23])[CH:5]=[CH:6][CH:7]=1.Br[CH2:31][C:32]1[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=1>>[C:24]1([C:22]([C:9]2[CH:10]=[N:11][C:12]3[C:17]([C... | O=C(c1ccccc1)c1cnc2c(C(F)(F)F)cccc2c1-c1cccc(O)c1 | BrCc1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from [4-(3-hydroxyphenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone and 4-Bromomethyl-pyridine following the procedure of Example 478: MS (ESI) m/z 485. | O=C(c1ccccc1)c1cnc2c(C(F)(F)F)cccc2c1-c1cccc(OCc2ccncc2)c1 | null | null | null |
395,053 | ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | null | 1998-01-01T00:03:00 | true | Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[Mg].C(=O)([O:15][CH2:16][CH3:17])OCC.Cl>C(OCC)C>[CH2:2]([C:16]([CH2:17][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[OH:15])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9] | CCCCCCCCBr | CCOC(=O)OCC | null | Cl | [Mg] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | 30 | 1 | This compound may be prepared in the following manner. Three moles of 1-bromooctane are slowly added to 3 moles of magnesium turnings in 0.6 liters of anhydrous ethyl ether (nitrogen atmosphere). One mole of diethyl carbonate in 0.151 anhydrous ethyl ether is slowly added to the mixture. The mixture is stirred for one ... | CCCCCCCCC(O)(CCCCCCCC)CCCCCCCC | null | null | null |
568,109 | ord_dataset-5c8a417a8ba04cf0b7f78b9db9af1d01 | null | 2002-01-01T00:10:00 | true | Br[C:2]1([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[C:7](=[O:8])[NH:6][C:5](=[O:9])[NH:4][C:3]1=[O:10].[OH:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>CO>[O:17]([C:14]1[CH:15]=[CH:16][C:11]([C:2]2([CH:28]3[CH2:29][NH:30][CH2:31][CH2:32][N:... | O=C1NC(=O)C(Br)(c2ccc(Oc3ccccc3)cc2)C(=O)N1 | OCCN1CCNCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 2 | A solution of 5-Bromo-5-(4′-phenoxyphenyl)barbituric Acid (50 mg) in 0.2 ml of methanol is added dropwise with a solution of N-(2-hydroxyethyl)piperazine (52 mg) in 0.6 ml of methanol and the mixture is stirred for 2 hours. The white precipitate is recovered by filtration and dried under vacuum at 60° C. overnight. 42.... | O=C1NC(=O)C(c2ccc(Oc3ccccc3)cc2)(C2CNCCN2CCO)C(=O)N1 | null | 75.3 | null |
571,875 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]3[CH:21]=2)=[CH:8][C:7]=1[CH3:22].[CH2:23]([NH:27][CH2:28][CH2:29][CH2:30]C)[CH2:24][CH2:25]C>>[CH2:23]([N:27]([CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[C:19]([CH3:20... | Cc1cc(-c2cn3cccc(C)c3n2)ccc1OCCCCl | CCCCNCCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The product of Step C (3.0 g) and dibutylamine (10.0 mL) were heated at reflux temperature for 18 hours. The reaction was evaporated and the residue was purified via silica gel chromatography (dichloromethane/methanol) to give the title compound. | CCCN(CCC)CCCOc1ccc(-c2cn3cccc(C)c3n2)cc1C | null | null | null |
1,525,750 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:30][CH3:31])=[C:17]([O:20][CH2:21][CH2:22][CH2:23][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2]>C(OCC)(=O)C>[CH2:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:30][CH... | C#Cc1cccc(Nc2ncnc3cc(OC)c(OCCCN4CCOCC4)cc23)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 67.5 | null | Into a three liter three necked round bottomed flask equipped with a mechanical stirrer, reflux-condenser and thermometer socket were charged ethyl acetate (2000 ml), followed by N-(3-ethynylphenyl)-7-methoxy-6-[3-(4-morpholinyl)propoxy]-4-quinazolinamine (25 g) obtained from the process described in the above given Ex... | CCc1cccc(Nc2ncnc3cc(OC)c(OCCCN4CCOCC4)cc23)c1 | null | 83 | null |
1,400,982 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]([CH3:13])[CH3:12])[CH:9]=2)[N:4]([CH3:14])[N:3]=1.C([Mg]Cl)(C)C.[CH2:20]([Sn:24]([CH2:30][CH2:31][CH2:32][CH3:33])([CH2:26][CH2:27][CH2:28][CH3:29])Cl)[CH2:21][CH2:22][CH3:23]>C1COCC1>[CH:11]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]([CH3:14])[N:3]=[C:2]2[Sn:24]([CH... | CC(C)c1ccc2c(c1)c(I)nn2C | CCCC[Sn](Cl)(CCCC)CCCC | null | CC(C)[Mg]Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | -16 | 0.33 | To a stirred solution of 3-iodo-5-isopropyl-1-methyl-1H-indazole (0.3 g, crude) in 100 mL of dry THF at −16° C. under nitrogen was added i-PrMgCl (0.69 mL, 1.38 mmol, 2M in THF) drop-wise. Then the mixture was stirred at −16° C. for 20 minutes. Tributylchlorostannane (0.39 g, 1.2 mmol) was added slowly and the mixture ... | CCCC[Sn](CCCC)(CCCC)c1nn(C)c2ccc(C(C)C)cc12 | null | null | null |
1,405,139 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:11]([CH3:21])[C:12](=[O:20])[C:13]([CH3:19])=[CH:14][C:15]=1[C:16]([OH:18])=[O:17].O[N:23]1[C:27](=[O:28])[CH2:26][CH2:25][C:24]1=[O:29].C1CCC(N=C=NC2CCCCC2)CC1>O1CCOCC1>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:11]([CH3:21])[C:12... | O=C1CCC(=O)N1O | Cc1cc(C(=O)O)c(Nc2ccc(I)cc2F)n(C)c1=O | null | C(=NC1CCCCC1)=NC1CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 25 | 16 | A 250 ml round-bottom flask was charged with 2-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid (2.0 g, 5.00 mmol) and dioxane (100 mL). To the resulting suspension was added 1-hydroxypyrrolidine-2,5-dione (0.63 g, 5.5 mmol) and DCC (0.63 g, 5.5 mmol). The reaction mixture was stirr... | Cc1cc(C(=O)ON2C(=O)CCC2=O)c(Nc2ccc(I)cc2F)n(C)c1=O | null | 84.1 | null |
219,533 | ord_dataset-6cb04513a4a244c0b612b566096f4b3d | null | 1990-01-01T00:12:00 | true | [N+](C1C=CC([O:10][C:11](=O)/[CH:12]=[CH:13]/[CH:14]=[C:15]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)=CC=1)([O-])=O.[N:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][NH2:45])[CH:34]=1>O1CCCC1>[CH3:31][... | NCCCCCCc1cccnc1 | COc1cccc(C(=C/C=C/C(=O)Oc2ccc([N+](=O)[O-])cc2)c2cccc(OC)c2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | As in Example 134. a solution of (E)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester (3.0 g) and 3-pyridinehexanamine (1.25 g) in tetrahydrofuran (20 mL) was stirred for 1.5 hours at room temperature and was then worked up in the usual manner. The product was purified by HPLC (ethyl acetate) and trit... | COc1cccc(C(=C/C=C/C(=O)NCCCCCCc2cccnc2)c2cccc(OC)c2)c1 | null | 76.4 | null |
785,197 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | C([O:14][C:15]1[C:16]2[C:35](=[O:36])[N:34]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)[CH2:33][C:17]=2[C:18]([O:25][S:26]([C:29]([F:32])([F:31])[F:30])(=[O:28])=[O:27])=[C:19]2[C:24]=1[N:23]=[CH:22][CH:21]=[CH:20]2)(C1C=CC=CC=1)C1C=CC=CC=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[F:44][C:41]1[CH:40]=[C... | O=C1c2c(c(OS(=O)(=O)C(F)(F)F)c3cccnc3c2OC(c2ccccc2)c2ccccc2)CN1Cc1ccc(F)cc1 | null | null | CC[SiH](CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a solution of trifluoro-methanesulfonic acid 9-benzhydryloxy-7-(4-fluoro-benzyl)-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester 46 (28 mg, 0.045 mmol) dissolved in dichloromethane (2 mL) was added trifluoroacetic acid (100 μl) and triethylsilane (200 μl). The reaction mixture was stirred at room temperature ... | O=C1c2c(c(OS(=O)(=O)C(F)(F)F)c3cccnc3c2O)CN1Cc1ccc(F)cc1 | null | 66.7 | null |
1,618,120 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [CH2:1]([C:8]1[C:13](=[O:14])[CH:12]=[C:11]([CH3:15])[NH:10][C:9]=1[CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[I:17]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[CH2:1]([C:8]1[C:13](=[O:14])[C:12]([I:17])=[C:11]([CH3:15])[NH:10][C:9]=1[CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7] | CCCCCCCc1c(C)[nH]c(C)cc1=O | II | null | O=S([O-])([O-])=S | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 70 | 7 | To a solution of 3 (100 mg, 0.45 mmol) in acetonitrile (2.5 mL) was added ceric ammonium nitrate (25 mg, 0.045 mmol) followed by iodine (126 mg, 0.495 mmol). The reaction mixture was stirred at 70° C. under nitrogen for 7 h. After completion of the reaction, the mixture was cooled to room temperature and treated with a... | CCCCCCCc1c(C)[nH]c(C)c(I)c1=O | null | null | null |
1,270,501 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12](=[O:15])[NH:13][CH:14]=2)=[CH:5][CH:4]=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23]Cl)=[CH:19][N:18]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[Cl:16][C:17]1[N:18]=[CH:19][C:20]([CH2:23][N:13]2[CH:14]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=... | COc1ccc(-c2ccc(=O)[nH]c2)cc1 | ClCc1ccc(Cl)nc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | null | 5-(4-Methoxyphenyl)pyridine-2(1H)-one (4.20 mmol, 0.85 g), 2-chloro-5-(chloromethyl)pyridine (1.5 eq, 6.30 mmol, 1.02 g), K2CO3 (2 eq, 8.40 mmol, 1.17 g) in THF (10 mL) were heated at 70° C. for 2 hours. Then, the reaction was cooled to room temperature. The suspension was filtered off and the filtrate was evaporated u... | COc1ccc(-c2ccc(=O)n(Cc3ccc(Cl)nc3)c2)cc1 | null | 75.8 | null |
1,593,630 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [Cl:1][C:2]1[N:7]=[C:6](O)[N:5]2[CH:9]=[C:10]([CH2:12][N:13]([CH3:15])[CH3:14])[N:11]=[C:4]2[CH:3]=1.P(Cl)(Cl)([Cl:18])=O>>[Cl:18][C:6]1[N:5]2[CH:9]=[C:10]([CH2:12][N:13]([CH3:15])[CH3:14])[N:11]=[C:4]2[CH:3]=[C:2]([Cl:1])[N:7]=1 | CN(C)Cc1cn2c(O)nc(Cl)cc2n1 | O=P(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to Example 11A, 30 mg (18% of theory) of the product are obtained from 131 mg (0.58 mmol) of 7-chloro-2-[(dimethylamino)methyl]imidazo[1,2-c]pyrimidin-5-ol (Example 98A) by reaction with phosphoryl chloride. | CN(C)Cc1cn2c(Cl)nc(Cl)cc2n1 | null | null | null |
1,192,394 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | [C:1](Cl)(=[O:3])[CH3:2].[CH2:5]([O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[C:18](=[O:29])[N:17]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=1)[C:16]2=[O:41])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CCN(CC)CC>C(C... | COc1ccc(Cn2c(=O)c3cc(OCc4ccccc4)ccc3n(C3CCNCC3)c2=O)cc1OC | CC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 0 | 8 | 0.14 g of acetyl chloride is added to a mixture of 0.6 g of 6-(benzyloxy)-3-(3,4-dimethoxybenzyl)-1-(piperidin-4-yl)quinazoline-2,4(1H,3H)-dione obtained according to stage 1.6 and 0.24 g of NEt3 in 10 ml of DCM cooled to 0° C. The mixture is stirred at AT overnight. It is washed twice with a saturated NH4Cl solution a... | COc1ccc(Cn2c(=O)c3cc(OCc4ccccc4)ccc3n(C3CCN(C(C)=O)CC3)c2=O)cc1OC | null | 98.4 | null |
225,835 | ord_dataset-67612e25ea9d4b29966a776893a43d59 | null | 1991-01-01T00:04:00 | true | CC(OC(=O)[NH:7][CH:8]([C:13]([N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]([CH2:24][CH:25]2[N:31]=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:29]3[CH:38]=[CH:39][CH:40]=[CH:41][C:28]=3[NH:27][C:26]2=[O:42])[CH2:16]1)=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])(C)C.[ClH:44]>C(OCC)(=O)C>[ClH:44]... | CC(C)CC(NC(=O)OC(C)(C)C)C(=O)N1CC(CC2N=C(c3ccccc3)c3ccccc3NC2=O)c2ccccc21 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | The procedure of Example 2 was carried out in which (1-[(3-[(2,3-dihydro-2-oxo-5-phenyl-1,4-benzodiazepin-3-yl)methyl]-2,3-dihydro-1H-indol-1-yl) carbonyl]-3-methylbutyl]-carbamic acid-1,1-dimethylethyl ester was reacted with excess HCl gas in ethyl acetate at 0° C. to give the title compound as a foam. | CC(C)CC(N)C(=O)N1CC(CC2N=C(c3ccccc3)c3ccccc3NC2=O)c2ccccc21 | null | null | null |
93,742 | ord_dataset-62e11cab5a6e47d89878616c244e20ef | null | 1982-01-01T00:05:00 | true | [C:1]([C:4]1[CH:9]=[C:8]([C:10](=[O:12])[CH3:11])[C:7]([OH:13])=[CH:6][C:5]=1[NH2:14])(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:21](Br)[CH:22]=[CH2:23].O>CN(C)C=O>[CH2:23]([O:13][C:7]1[CH:6]=[C:5]([C:4]([C:1](=[O:3])[CH3:2])=[CH:9][C:8]=1[C:10](=[O:12])[CH3:11])[NH2:14])[CH:22]=[CH2:21] | CC(=O)c1cc(C(C)=O)c(O)cc1N | C=CCBr | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | Treatment of the product of step (b) (1.5 g) with K2CO3 (1 equivalent) and allyl bromide (2 equivalents) in dimethylformamide (20 ml) at 70° C. for 21/2 hours followed by dilution with water at 70° C. afforded the sub-title product, as a pale yellow solid (83%) mp 131°-134°. | C=CCOc1cc(N)c(C(C)=O)cc1C(C)=O | null | null | null |
840,759 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | Br[C:2]1[N:3]([CH3:23])[C:4]([C:13]2[S:14][C:15]3[N:16]=[CH:17][N:18]=[C:19]([NH2:22])[C:20]=3[N:21]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[CH3:24][Si:25]([C:28]#[CH:29])([CH3:27])[CH3:26].C(N(CC)CC)C>CN(C=O)C.[Cu]I>[CH3:23][N:3]1[C:4]([C:13]2[S:14][C:15]3[N:16]=[CH:17][N:18]=[C:19]([NH2:22])[C:2... | Cn1c(Br)nc(-c2ccccc2)c1-c1nc2c(N)ncnc2s1 | C#C[Si](C)(C)C | null | [Cu]I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | 2-(2-Bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine (Example 26) (52 mg), PdCl2dppf (10 mg), copper(I) iodide (2 mg), trimethylsilyl acetylene (0.11 mL) and triethylamine (0.2 mL) were heated in DMF (4 mL) at 80° C. for 1 hour under an inert atmosphere. The reaction mixture was concentra... | Cn1c(C#C[Si](C)(C)C)nc(-c2ccccc2)c1-c1nc2c(N)ncnc2s1 | null | 100 | null |
605,756 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [C:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14](/[C:18](/[CH3:25])=[CH:19]\[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>[Pd].C(O)C>[C:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([CH:18]([CH3:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15][CH:... | CCOC(=O)/C=C(/C)c1ccc2c(c1)CCCN2C(=O)OC(C)(C)C | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of ethyl 3-(1-boc-1,2,3,4-tetrahydro-quinolin-6-yl)crotonate [9 g, Reference Example 7(c)] and 5% palladium on charcoal (2.5 g) in ethanol (250 ml) was hydrogenated at room temperature and pressure overnight. The spent catalyst was removed by filtration through Celite and the filtrate was evaporated to give t... | CCOC(=O)CC(C)c1ccc2c(c1)CCCN2C(=O)OC(C)(C)C | null | 100.5 | null |
1,506,677 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | CC([O-])(C)C.[K+].Cl[C:8]1[CH:13]=[CH:12][N:11]=[C:10]2[CH:14]=[CH:15][S:16][C:9]=12.COC(=O)CC[S:22][C:23]1[CH:24]=[C:25]([O:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:26]([NH:29][C:30]2[S:31][CH:32]=[C:33]([CH2:35][CH:36]3[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38]... | COC(=O)CCSc1cnc(Nc2nc(CC3CCN(C(=O)OC(C)(C)C)CC3)cs2)c(Oc2ccccc2)c1 | Clc1ccnc2ccsc12 | null | CC(C)(C)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | null | 2 | Added potassium 2-methylpropan-2-olate (0.443 g, 3.95 mmol) to a solution of 7-chlorothieno[3,2-b]pyridine (0.268 g, 1.58 mmol) and tert-butyl 4-((2-(5-(3-methoxy-3-oxopropylthio)-3-phenoxypyridin-2-ylamino)thiazol-4-yl)methyl)piperidine-1-carboxylate (0.77 g, 1.32 mmol) in DMSO (8 mL). The reaction was stirred for two... | CC(C)(C)OC(=O)N1CCC(Cc2csc(Nc3ncc(Sc4ccnc5ccsc45)cc3Oc3ccccc3)n2)CC1 | null | 97.1 | null |
171,873 | ord_dataset-7860c6f563014da8948ede63b7110bde | null | 1988-01-01T00:05:00 | true | [CH3:1][C:2]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:25])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:24])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])=[CH:3][C:4]([NH:6][CH2:7][CH2:8][OH:9])=[O:5]>[Pd].C(O)C>[CH3:1][CH:2]([CH2:10][CH2:11][CH2:12][CH:13]([CH3:25])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:24])[CH2:18][CH2:19][CH2:20]... | CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CC(=O)NCCO | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | 6.5 g of N-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenoyl)-ethanolamine obtained in Example 1 was hydrogenated in the presence of a catalyst composed of palladium on carbon in 40 ml of ethanol. The ethanol layer was then separated from the catalyst and the solvent was distilled off to afford 6.7 g (yield 94%) of t... | CC(C)CCCC(C)CCCC(C)CCCC(C)CC(=O)NCCO | null | 100.7 | null |
1,549,573 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [CH3:1][N:2]([C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:26]=1[NH:25][C:24]([C:27]1[S:28][CH:29]=[CH:30][N:31]=1)=[CH:23]2)[S:3]([C:6]1[CH:10]=[CH:9][S:8][C:7]=1[CH2:11][S:12][CH2:13][C:14]([O:16]C)=[O:15])(=[O:5])=[O:4].[OH-].[Na+]>CO.O1CCCC1>[CH3:1][N:2]([C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:26]=1[NH:25][C:24]([C:27]1[... | COC(=O)CSCc1sccc1S(=O)(=O)N(C)c1cccc2cc(-c3nccs3)[nH]c12 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 3 | To a solution of methyl ({[3-({methyl[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]amino}sulfonyl)-2-thienyl]methyl}thio)acetate (300 mg) in methanol (2 mL) and tetrahydrofuran (2 mL) was added 1N aqueous sodium hydroxide solution (2 mL) at room temperature, and the mixture was stirred for 3 hr. The reaction mixture was concentr... | CN(c1cccc2cc(-c3nccs3)[nH]c12)S(=O)(=O)c1ccsc1CSCC(=O)O | null | 94.7 | null |
662,909 | ord_dataset-5a3d853c53674888a5691dce2e398792 | null | 2005-01-01T00:03:00 | true | [F:1][C:2]([F:20])([F:19])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[CH:12]=[CH:13][NH:14]3)=[CH:6][CH:5]=1.[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(O)(=[O:44])C>CC(O)(C)C.C(O)C.C(O)(=O)C.[Zn]>[F:20][C:2]([F:1])([F:19])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:... | FC(F)(F)Oc1ccc(-c2cccc3[nH]ccc23)cc1 | CC(=O)O | null | [Br-] | [Zn] | c1cc[nH+]cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CC(C)(C)O | null | null | null | null | null | null | null | null | null | 27 | 3 | To the suspension of 4-(4-trifluoromethoxy-phenyl)-1H-indole (4.93 g, 17.78 mmol) in t-BuOH-ethanol-acetic acid (3:2:1) (261 mL) was added pyridinium tribromide (17.06 g, 53.34 mmol)) portionwise. The mixture was stirred at 27° C. for 3 hours, and then to the mixture was added acetic acid (105 mL). Zinc dust was added ... | O=C1Cc2c(cccc2-c2ccc(OC(F)(F)F)cc2)N1 | null | 39 | null |
801,607 | ord_dataset-56a22bc0c3b14f87b9aa3f2fc6488ee7 | null | 2007-01-01T00:12:00 | true | Br[C:2]1[C:10]2[C:5](=[C:6]([C:11]([O:13]CC)=[O:12])[CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[C:16]([Cu])#[N:17]>CN1C(=O)CCC1>[C:16]([C:2]1[C:10]2[C:5](=[C:6]([C:11]([OH:13])=[O:12])[CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1)#[N:17] | N#C[Cu] | CCOC(=O)c1cccc2c(Br)c[nH]c12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | null | 120 | 3 | 7 g of ethyl 3-bromoindole-7-carboxylate are dissolved in 70 g of NMP, and 4 g of CuCN are added. The mixture is heated to 100-140° C. with stirring. After 3 hours, the mixture is subjected to conventional work-up, giving 3-cyanoindole-7-carboxylic acid. | N#Cc1c[nH]c2c(C(=O)O)cccc12 | null | null | null |
1,316,678 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | C([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]([O:20][CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1)=[O:19])C1C=CC=CC=1>CO.[Pd]>[OH:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]([O:20]... | CC(C)(C)OC(=O)N1CCC(COC(=O)[C@@H]2CC[C@@H]3CN2C(=O)N3OCc2ccccc2)CC1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 8 | To a mixture of the product of Step 1 (100 mg, 0.211 mmol) in methanol was added 10% palladium on carbon (6.74 mg). The reaction mixture was stirred under an atmosphere of hydrogen (balloon) overnight then filtered. The filtrate was concentrated under vacuum to afford the title compound which was used without purificat... | CC(C)(C)OC(=O)N1CCC(COC(=O)[C@@H]2CC[C@@H]3CN2C(=O)N3O)CC1 | null | null | null |
431,576 | ord_dataset-8cbb58558c904b2b85fa7a1b084a0de9 | null | 1999-01-01T00:06:00 | true | [F:1][C:2]1[CH:17]=[CH:16][C:5]([CH:6]=[N:7][C:8]2[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C[Si]([C:22]#[N:23])(C)C>>[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH:6]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][CH:9]=2)[C:22]#[N:23])=[CH:4][CH:3]=1 | CSc1ccc(N=Cc2ccc(F)cc2)cc1 | C[Si](C)(C)C#N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following a procedure similar to that described in Example 1(ii), but using N-(4-fluorobenzylidene)-4-methylthioaniline [prepared as described in step (i) above] and trimethylsilyl cyanide as starting materials, the title compound was obtained as a pale yellow powder (yield 96%). | CSc1ccc(NC(C#N)c2ccc(F)cc2)cc1 | null | null | null |
192,407 | ord_dataset-11b3c3b41eda49e196ec983a65d3b2c0 | null | 1989-01-01T00:07:00 | true | [CH2:1]([O:3][C:4]([N:6]1[C:10]2=[CH:11][S:12][CH:13]=[C:9]2[N:8]=[C:7]1[S:14][CH2:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][N:17]=1)=[O:5])[CH3:2].C(=O)(O)[O-:25].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4]([N:6]1[C:10]2=[CH:11][S:12][CH:13]=[C:9]2[N:8]=[C:7]1[S:14]([CH2:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:... | CCOC(=O)n1c(SCc2cc(OC)ccn2)nc2cscc21 | O=C([O-])O | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | To 750 mg (2.1 mmol) of 1-ethoxycarbonyl-2-(4-methoxy-2-picolylmercapto)-1H-thieno[3,4-d]imidazole in 30 ml of methylene chloride and 25 ml of 0.5 N aqueous sodium bicarbonate solution were added dropwise, with stirring, initially 420 mg (2.1 mmol) and then a further 210 mg (1.05 mmol) of 3-chloroperbenzoic acid CH2Cl2... | CCOC(=O)n1c(S(=O)Cc2cc(OC)ccn2)nc2cscc21 | null | null | null |
926,382 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH:16][NH2:17])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(O[C:22](=[NH:24])[CH3:23])C.CCN(CC)CC>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[NH:24][C:22]([CH3:23])=[N:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2] | CCOC(C)=N | CC(C)(C)OC(=O)N1CCC(C(=O)NN)CC1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CN(C)C=O | null | null | null | null | null | null | null | null | null | 100 | null | 4-Hydrazinocarbonyl-piperidine-1-carboxylic acid tert-butyl ester (1.19 g, 5 mmol) was mixed with ethylacetimidate hydrochloride (0.91 g, 7 mmol) in DMF (5 ml) and Et3N (2 ml, 15 mmol) was added. The reaction was stirred for 1 h after which time the DMF was evaporated, the residue redissolved in AcOH and 0.5 g of ammon... | Cc1nnc(C2CCN(C(=O)OC(C)(C)C)CC2)[nH]1 | null | 10.5 | null |
1,721,979 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [F:1][C:2]1[C:11]2=[CH:12][C:13]([F:15])=[CH:14][C:9]3=[C:10]2[C:4](=[N:5][NH:6][C:7]2[C:8]3=[CH:16][N:17]([CH3:26])[CH2:18][C:19]=2[C:20]2[CH2:21][CH2:22][NH:23][CH2:24][CH:25]=2)[CH:3]=1.C(N(CC)CC)C.Cl[CH2:35][C:36]([N:38]([CH3:40])[CH3:39])=[O:37]>CN(C)C=O>[F:1][C:2]1[C:11]2=[CH:12][C:13]([F:15])=[CH:14][C:9]3=[C:10... | CN(C)C(=O)CCl | CN1C=C2C(=C(C3=CCNCC3)C1)NN=C1C=C(F)c3cc(F)cc2c31 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CN(C)C=O | null | null | null | null | null | null | null | null | null | 70 | null | To a suspension of Example 48 (100 mg, 0.284 mmol) in N,N-dimethylformamide (4 mL) was added triethylamine (0.237 mL, 1.703 mmol) and 2-chloro-N,N-dimethylacetamide (41.4 mg, 0.341 mmol) and the mixture was heated at 70° C. for 3 hours. After cooling, the mixture was partitioned between ethyl acetate and brine and the ... | CN1C=C2C(=C(C3=CCN(CC(=O)N(C)C)CC3)C1)NN=C1C=C(F)c3cc(F)cc2c31 | null | null | null |
23,718 | ord_dataset-fcf7c02bbb814fe696760b5fbfee16bb | null | 1977-01-01T00:05:00 | true | O=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[NH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>>[N:16]1([CH2:15][CH2:14][NH:13][CH2:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1 | NCCN1CCNCC1 | O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The product was made from D-glucose and N-(β-aminoethyl)-piperazine comparable as in Example A. A resin-like, pale pink product was obtained. | OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CNCCN1CCNCC1 | null | null | null |
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