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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
392,927 | ord_dataset-4bc8addcf9cf4845817557760d62d5b5 | null | 1998-01-01T00:02:00 | true | [NH2:1][C:2]1[NH:3][C:4](=[O:19])[C:5]2[NH:10][CH:9]=[C:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3Cl)[C:6]=2[N:7]=1.O.NN>C(O)C.[Pd]>[NH2:1][C:2]1[NH:3][C:4](=[O:19])[C:5]2[NH:10][CH:9]=[C:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[N:7]=1 | Nc1nc2c(Cc3ccccc3Cl)c[nH]c2c(=O)[nH]1 | null | null | [Pd] | NN | 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 | A solution of 2-amino-3,5-dihydro-7-(2-chlorophenylmethyl)-4H-pyrrolo[3,2-d]pyrimidin-4-one (0.5 g, 1.8 mmol) in hot ethanol (80 mL) is treated with 30% Pd-C (1.0 g) under N2 and then hydrazine monohydrate (1.5 mL) is added dropwise during a period of 10 minutes. The reaction mixture is held at reflux for 16 hours and ... | Nc1nc2c(Cc3ccccc3)c[nH]c2c(=O)[nH]1 | null | null | null |
516,881 | ord_dataset-a495451286334c5c9bbcbd48a00c1350 | null | 2001-01-01T00:09:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[H-].[Na+].[C:21]([N:25]=[C:26]=[O:27])([CH3:24])([CH3:23])[CH3:22]>O1CCCC1>[C:21]([NH:25][C:26](=[O:27])[O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([CH:15]... | CC(C)(C)N=C=O | O=Cc1ccc(OCCc2ccc(O)cc2)cc1 | null | [H-] | [Na+] | 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 | 0 | null | 0.5 g (2.1 mmole) 4-[2-(4-hydroxyphenyl)ethoxy]benzaldehyde was dissolved in tetrahydrofuran, cooled to 0° C. and 0.092 g (2.1 mmole) sodium hydride in tetrahydrofuiran was added. The reaction mixture was stirred until gas development ceased, then 0.4 g (4 mmole) tert-butyl isocyanate in tetrahydrofuran was added and t... | CC(C)(C)NC(=O)Oc1ccc(CCOc2ccc(C=O)cc2)cc1 | null | 83.7 | null |
1,646,786 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[C:10]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][N:11]=1.C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][N:11]=2)=[CH:4][CH:3]=1 | Brc1ccc(I)cn1 | Oc1ccc(F)cc1 | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 120 | 4 | A mixture of 4-fluorophenol (1.12 g, 10 mmol), 2-bromo-5-iodopyridine (2.84 g, 10 mmol) and Cs2CO3 (3.83 g, 10 mmol) in DMF was stirred at 120° C. for 4 hrs. The reaction was worked up with EtOAc to give 2-(4-fluoro-phenoxy)-5-iodo-pyridine which was used for next step without further purification (crude yield 100%, ye... | Fc1ccc(Oc2ccc(I)cn2)cc1 | null | null | null |
1,598,281 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH:11]4[CH2:17][N:15]([CH2:16][C:5]=3[C:4]=2[CH:3]=1)[CH2:14][CH2:13][CH2:12]4.[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[CH2:24])=[CH:21][CH:20]=1>>[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][CH2:24][N:7]2[C:8]3[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][C:4]=3[C:5]3[CH2:16][N:... | Cc1ccc2[nH]c3c(c2c1)CN1CCCC3C1 | C=Cc1ccc(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 coupling of 10-methyl-1,3,4,5,6,7-hexahydro-2,6-methanoazocino[4,3-b]indole (245.1 mg, 1.083 mmol; Example 201) and 4-chlorostyrene (256.3 mg, 1.709 mmol, Aldrich) was performed as described in Example 202, except that the material was purified by reverse-phase HPLC [Waters XBridge C18 5 μm OBD column, 30×100 mm, f... | Cc1ccc2c(c1)c1c(n2CCc2ccc(Cl)cc2)C2CCCN(C1)C2 | null | null | null |
1,297,525 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | I[C:2]1[C:3]([CH3:12])=[N:4][N:5]([CH2:7][C:8]([CH3:11])([OH:10])[CH3:9])[CH:6]=1.C1COCC1.C([Mg]Cl)(C)C.CO[B:25]1[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]1.[NH4+].[Cl-]>>[CH3:9][C:8]([OH:10])([CH3:11])[CH2:7][N:5]1[CH:6]=[C:2]([B:25]2[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26... | Cc1nn(CC(C)(C)O)cc1I | COB1OC(C)(C)C(C)(C)O1 | null | CC(C)[Mg]Cl | [Cl-] | [NH4+] | 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 | 1 | A solution of 1-(4-iodo-3-methyl-1H-pyrazol-1-yl)-2-methylpropan-2-ol (250.0 mg, 0.8925 mmol) in THF (10 mL, 200 mmol) was added 2 M of isopropylmagnesium chloride in THF (1.339 mL, 2.678 mmol) at rt, and the reaction was allowed to stir for 1 h. 2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.5850 mL, 3.570 mmol)... | Cc1nn(CC(C)(C)O)cc1B1OC(C)(C)C(C)(C)O1 | null | null | null |
1,275,159 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [N-:1]=[N+:2]=[N-:3].[Na+].Br[CH:6]([C:8]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=2[CH3:22])[C:12]2[N:23]=[C:24]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[S:25][C:11]=2[C:10](=[O:32])[N:9]=1)[CH3:7]>CN(C)C=O.O>[N:1]([CH:6]([C:8]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21... | Cc1c(Cl)cccc1Cn1c(C(C)Br)nc(=O)c2sc(N3CCOCC3)nc21 | [N-]=[N+]=[N-] | null | [Na+] | null | 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 | 65 | null | To a solution of sodium azide (20.16 mg, 0.310 mmol) in N,N-Dimethylformamide (DMF) (1.5 mL) was added 5-(1-bromoethyl)-4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (100 mg, 0.207 mmol) in N,N-Dimethylformamide (DMF) (1.5 mL). The reaction was heated to 65° C. for 2 hr, a... | Cc1c(Cl)cccc1Cn1c(C(C)N=[N+]=[N-])nc(=O)c2sc(N3CCOCC3)nc21 | null | 52.2 | null |
1,705,016 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH:24]1[CH2:30][CH:29]2[N:31]([C:32]3[C:33]4[C:48]([C:49]5[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=5)=[CH:47][S:46][C:34]=4[N:35]=[C:36]([N:38]4[CH2:42][CH2:41][CH:40]([C:43]([NH2:45])=[O:44])[CH2:39]4)[N:37]=3)[CH:26]([CH2:27][CH2:28]2)[CH2:25]1.S([O-])([O-])(=O)=S.[N... | NC(=O)C1CCN(c2nc(N3C4CCC3CC(O)C4)c3c(-c4ccccc4)csc3n2)C1 | null | null | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21 | O=S([O-])([O-])=S | [Na+] | 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 | 8 | Dess-Martin Periodinane (50 mg, 0.12 mmol) was added to a suspension of 1-[4-[3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl]-5-phenyl-thieno[2,3-d]pyrimidin-2-yl]pyrrolidine-3-carboxamide (40 mg, 0.089 mmol) in dichloromethane (4 mL). The mixture was stirred overnight at room temperature. Saturated aqueous sodium thiosulfate... | NC(=O)C1CCN(c2nc(N3C4CCC3CC(=O)C4)c3c(-c4ccccc4)csc3n2)C1 | null | 115.5 | null |
1,352,248 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | Cl[C:2]([O:4][CH3:5])=[O:3].[NH:6]1[CH2:11][CH2:10][CH:9]([N:12]2[CH2:16][CH2:15][C:14]3([CH2:21][CH2:20][CH2:19][N:18]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][N:23]=4)[CH2:17]3)[C:13]2=[O:32])[CH2:8][CH2:7]1.C(N(CC)C(C)C)(C)C.C(Cl)Cl>>[O:32]=[C:13]1[C:14]2([CH2:21][CH2:20][CH2:19][N:18]([C:2... | O=C1N(C2CCNCC2)CCC12CCCN(c1ccc(C(F)(F)F)cn1)C2 | COC(=O)Cl | null | null | null | null | 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 | null | 0.5 | Methyl chloroformate (4.4 μL, 0.000057 mol) was added to a solution of 2-piperidin-4-yl-7-[5-(trifluoromethyl)pyridin-2-yl]-2,7-diazaspiro[4.5]decan-1-one (18.3 mg, 0.0000478 mol) and N,N-diisopropylethylamine (27 μL, 0.00016 mol) in methylene chloride (1.0 mL, 0.016 mol); and the mixture was stirred for 0.5 h. The vol... | COC(=O)N1CCC(N2CCC3(CCCN(c4ccc(C(F)(F)F)cn4)C3)C2=O)CC1 | null | null | null |
911,627 | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | null | 2009-01-01T00:10:00 | true | CO[N:3]=[C:4]1[CH2:12][CH2:11][C:10]2[N:9]=[CH:8][CH:7]=[CH:6][C:5]1=2>C(O)(C(F)(F)F)=O.[Pd]>[N:9]1[C:10]2[CH2:11][CH2:12][CH:4]([NH2:3])[C:5]=2[CH:6]=[CH:7][CH:8]=1 | CON=C1CCc2ncccc21 | null | null | [Pd] | null | null | 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 | null | null | A solution of 6,7-dihydro-[1]pyrindin-5-one O-methyl-oxime (5.43 g, 33.5 mmol) and Pd/C (150 mg) in TFA were hydrogenated under 50 psi for 14 hours. Filtration via celite and concentration afforded the title amine. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ 1.66-1.77 (m, 2H), 2.17-2.27 (m, 2H), 2.45-2.50 (m, 1H), 3.... | NC1CCc2ncccc21 | null | null | null |
1,319,962 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | CO.C([O:10][C:11]1[CH:38]=[C:37]([N:39]([CH2:41][CH2:42][N:43]([CH3:45])[CH3:44])[CH3:40])[CH:36]=[CH:35][C:12]=1[C:13]([NH:15][C:16]1[CH:28]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:26]=[CH:25][C:17]=1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:14])C1C=CC=CC=1>[C].[Pd].C(Cl)(Cl)Cl>[CH3... | CN(C)CCN(C)c1ccc(C(=O)Nc2cc(-c3ccccc3)ccc2C(=O)OC(C)(C)C)c(OCc2ccccc2)c1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | 25 | 0.75 | To a methanol (3.0 mL) solution of the obtained tert-butyl 2-(2-(benzyloxy)-4-((2-(dimethylamino)ethyl)(methyl)amino)benzamido)-4-phenylbenzoate (0.071 g), 10% palladium-carbon (0.035 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 1 hour and 45 minutes. Methanol (2.0 mL) and chlo... | CN(C)CCN(C)c1ccc(C(=O)Nc2cc(-c3ccccc3)ccc2C(=O)OC(C)(C)C)c(O)c1 | null | 75 | null |
4,854 | ord_dataset-a5669edbeffe43bf8514c1bfede8f882 | null | 1976-01-01T00:04:00 | true | [CH2:1]([S:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([S:25](Cl)(=[O:27])=[O:26])[C:17]=1[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:29]>>[CH2:1]([S:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([S:25](=[O:27])(=[O:26])[NH2:29])[C:17]=1[O:18][C:19]1[CH:24... | N | O=C(O)c1cc(SCc2ccccc2)c(Oc2ccccc2)c(S(=O)(=O)Cl)c1 | 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 | 1 | 3-Benzylthio-5-chlorosulfonyl-4-phenoxybenzoic acid (0.6 g) is added to concentrated aqueous ammonia (10 ml). After 1 hour, the reaction mixture is heated on a steam-bath for 15 minutes, and crude 3-benzylthio-4-phenoxy-5-sulfamylbenzoic acid precipitated by addition of a 1 N hydrochloric acid until pH 2.5. The crude p... | NS(=O)(=O)c1cc(C(=O)O)cc(SCc2ccccc2)c1Oc1ccccc1 | null | null | null |
1,240,851 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | C([O:3][C:4](=[O:25])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:18][C:19]3[CH:24]=[N:23][CH:22]=[CH:21][N:20]=3)[CH:14]=[C:15]([CH2:16][CH3:17])[C:7]1=2)C.[Li+].[OH-].Cl>C1COCC1.O>[CH2:16]([C:15]1[C:7]2[CH:6]([CH2:5][C:4]([OH:25])=[O:3])[O:10][B:9]([OH:11])[C:8]=2[CH:12]=[C:13]([O:18][C:19]2[CH:24]=[N:23... | CCOC(=O)CC1OB(O)c2cc(Oc3cnccn3)cc(CC)c21 | 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 | 2 | To a solution of [4-ethyl-1-hydroxy-6-(pyrazin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.11 g, 0.32 mmol) in THF (4 mL) and H2O (2 mL) was added LiOH (0.040 g) at 0° C. The resulting mixture was stirred at room temperature for 2 hours then cooled to 0° C. and acidified to pH 3 with 6N ... | CCc1cc(Oc2cnccn2)cc2c1C(CC(=O)O)OB2O | null | 79.6 | null |
1,758,444 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | C([Li])CCC.[C:6](#[N:8])[CH3:7].[F:9][C:10]([F:17])([CH2:15][CH3:16])[C:11](OC)=[O:12]>C1COCC1>[F:9][C:10]([F:17])([CH2:15][CH3:16])[C:11](=[O:12])[CH2:7][C:6]#[N:8] | CCC(F)(F)C(=O)OC | CC#N | null | [Li]CCCC | 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 | -78 | 1 | A flame-dried flask was charged with 2.9 ml (4.6 mmol) of n-butyllithium solution (1.6 M in hexanes) in dry THF (14 ml) under inert gas atmosphere and cooled to −78° C. Next, 0.213 ml (4.06 mmol) acetonitrile were slowly added, and the resulting mixture was stirred for 1 h at −70° C. Then, 0.40 g (2.9 mmol) methyl 2,2-... | CCC(F)(F)C(=O)CC#N | null | null | null |
396,287 | ord_dataset-a4a191e812a64d0598ea918f047e8da7 | null | 1998-01-01T00:04:00 | true | [F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.[C:12](O)(=[O:14])[CH3:13]>[Fe]>[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[NH:8][C:12](=[O:14])[CH3:13] | O=[N+]([O-])c1ccc(O)cc1F | CC(=O)O | null | [Fe] | 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 | null | 373.3 mg of iron powder were added to a solution of 300 mg of 3-fluoro-4-nitrophenol [prepared as described in step (c) above] in 6 ml of glacial acetic acid. The resulting mixture was stirred under reflux for 6 hours, after which it was allowed to cool to room temperature. Ice-water was then added to the reaction mixt... | CC(=O)Nc1ccc(O)cc1F | null | 64 | null |
1,146,222 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:8]([O:20][C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[N:26]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[N:25]=[CH:24]3)[C@H:9]([CH2:11][O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH2:10])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:44][O:45][CH2:46][C:47](Cl)=[O:48]... | N[C@@H](COCc1ccccc1)C(Oc1ccc2c(cnn2-c2ccc(F)cc2)c1)c1cccc(F)c1 | COCC(=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 | 25 | 8 | (αS)-3-Fluoro-β-[[1-(4-fluorophenyl)-1H-indazole-5-yl]oxy]-α-[(phenylmethoxy)methyl]benzeneethanamine is synthesized in analogy to the sequence previously described in example 1: commercially available Boc-Ser(Bn)-OH is transformed into its Weinreb-amide. Reduction to the aldehyde with LiAl4, reaction with 3-fluorophen... | COCC(=O)N[C@@H](COCc1ccccc1)C(Oc1ccc2c(cnn2-c2ccc(F)cc2)c1)c1cccc(F)c1 | null | null | null |
900,537 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [CH2:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[C:18]1[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[C:25]([F:28])([F:27])[F:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:29][C:30]1[CH:31]=[CH:32][C:33]([OH:38])=[C:34]([CH:37]=1)[CH:35]=O>>[CH2:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([... | Nc1cccc(-c2c(Cc3ccccc3)cnc3c(C(F)(F)F)cccc23)c1 | O=Cc1cc(F)ccc1O | 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 {3-[3-benzyl-8-(trifluoromethyl)quinolin-4-yl]phenyl}amine and 5-fluoro-2-hydroxybenzaldehyde according to the procedure of step 1, Example 66. MS (ESI) m/z 503; MS (ESI) m/z 501. | Oc1ccc(F)cc1CNc1cccc(-c2c(Cc3ccccc3)cnc3c(C(F)(F)F)cccc23)c1 | null | null | null |
537,696 | ord_dataset-1884c7bf3d544afdb8d17b5d41b90a27 | null | 2002-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12](O)=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:23]=[CH:22][C:19](C=O)=[CH:18][CH:17]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](/[CH:11]=[CH:12]/[C:19]2[CH:22]=[CH:23][C:16]([Cl:15])=[CH:17][CH:18]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1 | O=Cc1ccc(Cl)cc1 | O=C(O)CS(=O)(=O)c1ccc(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 | A solution of 4-chlorophenyl sulfonylacetic acid (0.01 mol) and 4-chlorobenzaldehyde (0.01 mol) was subjected to Procedure 1. The title compound was obtained in 70-72% yield. | O=S(=O)(/C=C/c1ccc(Cl)cc1)c1ccc(Cl)cc1 | null | 70 | null |
175,315 | ord_dataset-4937da99a6a247eb90fa70f0d2eac3db | null | 1988-01-01T00:07:00 | true | S(Cl)([Cl:4])(=O)=O.[Cl:6][C:7]1[CH:18]=[C:17]([F:19])[C:16]([N:20]2[C:25](=[O:26])[CH:24]=[C:23]([CH3:27])[N:22]([CH3:28])[C:21]2=[O:29])=[CH:15][C:8]=1[C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10]>C(O)(=O)C>[Cl:6][C:7]1[CH:18]=[C:17]([F:19])[C:16]([N:20]2[C:25](=[O:26])[C:24]([Cl:4])=[C:23]([CH3:27])[N:22]([CH3:28])[... | O=S(=O)(Cl)Cl | Cc1cc(=O)n(-c2cc(C(=O)OC(C)C)c(Cl)cc2F)c(=O)n1C | 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 | 25 | 0.25 | 6.3 g of sulphuryl chloride are added dropwise with stirring to a solution of 15.0 g of isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-3,4-dimethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate in 100 ml of acetic acid at room temperature during 1 minute, during which the temperature rises to approx. 30° C. Then the reaction mixtu... | Cc1c(Cl)c(=O)n(-c2cc(C(=O)OC(C)C)c(Cl)cc2F)c(=O)n1C | null | null | null |
111,712 | ord_dataset-5237a168f9214b7ca3db5a1dc3e62d07 | null | 1983-01-01T00:12:00 | true | [CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([N:15]=[C:16]=[O:17])(=[O:14])=[O:13].[NH2:18][C:19]1[N:24]=[C:23]([Cl:25])[CH:22]=[C:21]([O:26][CH3:27])[N:20]=1>O1CCOCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([NH:15][C:16]([NH:18][C:19]1[N:24]=[C:2... | COCCOc1ccccc1S(=O)(=O)N=C=O | COc1cc(Cl)nc(N)n1 | null | null | 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 | 20 | 3 | A mixture consisting of 5.15 g of 2-methoxyethoxy-phenylsulfonyl isocyanate, 3.2 g of 2-amino-4-chloro-6-methoxy-pyrimidine and 70 ml of absolute dioxane is stirred for 3 hours at a temperature of 60°-70° C. The reaction mixture is cooled to a temperature of 20° C., treated with activated carbon, filtrated and evaporat... | COCCOc1ccccc1S(=O)(=O)NC(=O)Nc1nc(Cl)cc(OC)n1 | null | null | null |
635,535 | ord_dataset-de283386b8034acd99fba96d3c7d3227 | null | 2004-01-01T00:04:00 | true | C([O-])([O-])=O.[K+].[K+].Cl[CH2:8][CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)=[O:11].[CH3:19][CH:20]([CH3:36])[C:21]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:25]=1)=[O:22]>>[CH3:19][CH:20]([CH3:36])[C:21]([NH:23][C:24]1[CH:29]=[CH:28][C... | Cc1ccc(C(=O)CCCl)cc1 | CC(C)C(=O)Nc1cccc(C2CCNCC2)c1 | 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 | null | null | Procedure K (KI) and Scheme E (K2CO3) using 3-chloro-1-(4-methylphenyl)-1-propanone and 2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide: ESMS m/e: 393.2 (M+H)+. | Cc1ccc(C(=O)CCN2CCC(c3cccc(NC(=O)C(C)C)c3)CC2)cc1 | null | null | null |
1,059,244 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]2[C@@H:13]([CH2:21][OH:22])[O:12]1.C[Si](Cl)(C)C.[Br:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1.N>N1C=CC=CC=1.O>[Br:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([NH:1][C:2]... | O=C(Cl)c1ccc(Br)cc1 | CC1(C)O[C@@H]2[C@H](O1)[C@@H](CO)O[C@H]2n1cnc2c(N)ncnc21 | null | C[Si](C)(C)Cl | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | c1ccncc1 | null | null | null | null | null | null | null | null | null | 0 | 0.25 | [(3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methanol (0.400 g, 1.30 mmol) was dried by co-evaporation with pyridine, then suspended in dry pyridine (6.5 mL). TMSCl (0.330 mL, 2.60 mmol) was added and the mixture was stirred for 15 min. 4-Bromobenzoylchloride (0.342 g, 1.... | CC1(C)O[C@@H]2[C@H](O1)[C@@H](CO)O[C@H]2n1cnc2c(NC(=O)c3ccc(Br)cc3)ncnc21 | null | 47.9 | null |
793,642 | ord_dataset-744b04e8228742eb9aa4bde36f5dedf1 | null | 2007-01-01T00:10:00 | true | Cl[C:2]1[CH:3]=[C:4]([C:9]2[N:13]3[CH:14]=[CH:15][C:16]([C:19]([OH:22])([CH3:21])[CH3:20])=[C:17]([F:18])[C:12]3=[N:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].[O:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH:25]=[C:24]1B(O)O>>[O:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH:25]=[C:24]1[C:2]1[CH:3]=[C:4]([C:9]... | OB(O)c1cc2ccccc2o1 | CC(C)(O)c1ccn2c(-c3ccc(F)c(Cl)c3)cnc2c1F | 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-[3-(3-Chloro-4-fluorophenyl)-8-fluoroimidazo[1,2-α]pyridin-7-yl]-propan-2-ol and benzofuran-2-boronic acid were coupled in the same way as in Example 30 to give 2-{3-[3-(benzofuran-2-yl)-4-fluorophenyl]-8-fluoroimidazo[1,2-α]pyridin-7-yl}propan-2-ol as an off-white solid (6 mg, 3%): m/z (ES+) 405 [MH+]. | CC(C)(O)c1ccn2c(-c3ccc(F)c(-c4cc5ccccc5o4)c3)cnc2c1F | null | 3 | null |
1,216,977 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][N:7]=[C:6](Cl)[C:5]=1[Cl:11].[CH3:13][N:14](C=O)C>[C-]#N.[Zn+2].[C-]#N.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=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1... | CN(C)C=O | COC(=O)c1ccnc(Cl)c1Cl | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | [C-]#N | [Zn+2] | 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 | 190 | null | A microwave vial was charged with 2,3-dichloro-isonicotinic acid methyl ester (7.6 g, 36.9 mmol), zinc cyanide (4.75 g, 40.6 mmol), tetrakis(triphenylphosphine)palladium (1.0 g, 0.9 mmol) and DMF (37 mL), then capped, evacuated and backfilled with nitrogen. The reaction solution was subjected to microwave irradiation, ... | COC(=O)c1ccnc(C#N)c1Cl | null | 43 | null |
1,011,801 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:11]2[CH:12]=[C:13]([CH2:16][O:17][CH:18]3[CH:23]([C:24]4[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][O:33]S(C5C=CC(C)=CC=5)(=O)=O)=[CH:26][CH:25]=4)[CH2:22][CH2:21][N:20]([C:44]([O:46][CH2:47][C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)=[O:45])[CH2:19]3)[CH:14]=[CH:15][C:10]... | CCOc1ccccc1O | COCCCN1C(=O)COc2ccc(COC3CN(C(=O)OCc4ccccc4)CCC3c3ccc(OCCOS(=O)(=O)c4ccc(C)cc4)cc3)cc21 | 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 | Analogously to Method I, 0.420 g of benzyl 3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-4-{4-[2-(toluene-4-sulphonyloxy)ethoxy]phenyl}piperidinecarboxylate and 0.124 g of ethoxyphenol are reacted. The title compound is obtained as a dark yellow oil. Rf=0.16 (1:1 EtOAc-heptane); Rt=5.68. | CCOc1cccc(OCCOc2ccc(C3CCN(C(=O)OCc4ccccc4)CC3OCc3ccc4c(c3)N(CCCOC)C(=O)CO4)cc2)c1 | null | null | null |
1,769,399 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | Cl[CH2:2][C:3]1[C:4]([S:10][CH:11]([CH3:13])[CH3:12])=[N:5][CH:6]=[C:7]([CH3:9])[CH:8]=1.C[O:15][C:16](=[O:26])[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1>>[CH:11]([S:10][C:4]1[C:3]([CH2:2][O:25][C:22]2[CH:21]=[CH:20][C:19]([CH2:18][CH2:17][C:16]([OH:26])=[O:15])=[CH:24][CH:23]=2)=[CH:8][C:7]... | Cc1cnc(SC(C)C)c(CCl)c1 | COC(=O)CCc1ccc(O)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 | 3-Chloromethyl-2-isopropylsulfanyl-5-methyl-pyridine (0.052 g, 0.24 mmol) obtained in Step D of Preparation Example 30 and 3-(4-hydroxy-phenyl)-propionic acid methyl ester (0.043 g, 0.24 mol) obtained in Preparation Example 4 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain ... | Cc1cnc(SC(C)C)c(COc2ccc(CCC(=O)O)cc2)c1 | null | 55 | null |
474,029 | ord_dataset-cd531114850e4f239b2a3661044ae672 | null | 2000-01-01T00:08:00 | true | [OH:1][C:2]1[C:14]2[S:13][C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[C:10]=2[C:9]([C:19]2[CH:37]=[C:36]([Br:38])[C:22]([O:23][C@H:24]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:25]([O:27][CH3:28])=[O:26])=[C:21]([Br:39])[CH:20]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.[CH2:40](Br)[C:41]1[CH:46]=[CH:... | COC(=O)[C@@H](Cc1ccccc1)Oc1c(Br)cc(-c2c3ccccc3c(O)c3sc4ccccc4c23)cc1Br | BrCc1ccccc1 | null | null | null | 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 | null | 17 | To a solution of (R)-2-[4-(6-hydroxy-benzo[b]naphtho[2,3-d]thiophen-11-yl]-2,6-dibromo-phenoxy]-3-phenyl-propionic acid, methyl ester (0.50 g, 0.755 mmol) in dry N,N-dimethylformamide (5 mL) was added benzyl bromide (0.27 mL, 2.27 mmol, 3 eq) dropwise at room temperature under a dry nitrogen atmosphere. After stirring ... | COC(=O)C(Cc1ccccc1)Oc1c(Br)cc(-c2c3ccccc3c(OCc3ccccc3)c3sc4ccccc4c23)cc1Br | null | 100.7 | null |
1,171,745 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [Br-:1].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[F:22][C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[C:30](=[O:44])[CH2:31][C:32]1[CH:33]=[CH:34][C:35]2[N:36]([C:38]([CH:41]([CH3:43])[CH3:42])=[N:39][N:40]=2)[N:37]=1>C1COCC1.C(Cl)Cl>[Br:1][CH:31]([C:32]1[CH:33]=[CH:34][C:35]2[N:36]([C:38]([CH:... | [Br-] | CC(C)c1nnc2ccc(CC(=O)c3ccc(F)cc3F)nn12 | null | c1cc[nH+]cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 4 | Pyridinium tribromide (0.567 g, 1.77 mmol) was added to a solution of 1-(2,4-difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (0.488 g, 1.54 mmol; Preparation #K.1) in THF (6 mL) and the resulting reaction mixture was stirred at ambient temperature for about 4 h. The crude mixture was dilute... | CC(C)c1nnc2ccc(C(Br)C(=O)c3ccc(F)cc3F)nn12 | null | 100.2 | null |
1,380,460 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [C:1]([O:5][C:6]([C@@:8]1([CH2:23][CH2:24][CH2:25][O:26][Si](C(C)(C)C)(C)C)[CH:12]([F:13])[C:11](=[O:14])[N:10]([C@@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([O:5][C:6]([C@@:8]1([CH2:23][CH2:24][CH2:25]... | C[C@H](c1ccccc1)N1C[C@@](CCCO[Si](C)(C)C(C)(C)C)(C(=O)OC(C)(C)C)C(F)C1=O | null | null | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 21.5 | (3S)-3-[3-(tert-Butyldimethylsilyloxy)-1-propyl]-4-fluoro-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (8.15 g) was dissolved in tetrahydrofuran (25.0 mL). Acetic acid (22.0 mL) and tetrabutylammonium fluoride (1.0 M solution in tetrahydrofuran) (25.0 mL) were added under ice-cooling, and ... | C[C@H](c1ccccc1)N1C[C@@](CCCO)(C(=O)OC(C)(C)C)C(F)C1=O | null | 92.9 | null |
1,247,840 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21](O)=O)[C:9]=2[CH3:24])=[CH:4][CH:3]=1.Cl.[NH2:26][C:27]1([C:32]([NH2:34])=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19... | NC(=O)C1(N)CCCC1 | Cc1c(C(=O)O)nn(-c2ccc(Cl)cc2Cl)c1-c1ccc(Cl)cc1 | null | 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 | Compound 25 was synthesized from 4a (251 mg, 0.66 mmol) and 5j (140 mg, 0.98 mmol) as a white solid (140 mg, 45%) in a manner similar to that described in Example 53. 1H NMR (400 MHz, CDCl3) δ 7.40 (d, 1H), 7.32˜7.26 (m, 3H), 7.12 (s, 1H), 7.02 (d, 2H), 2.49 (m, 2H), 2.36 (s, 3H), 2.17 (m, 2H), 1.86 (m, 4H); ESMS m/z: ... | Cc1c(C2=NC3(CCCC3)C(=O)N2)nn(-c2ccc(Cl)cc2Cl)c1-c1ccc(Cl)cc1 | null | null | null |
1,751,786 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][N:13]2[C:18]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)([CH2:22][CH3:23])[C:19]([OH:21])=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:43][CH2:44][O:45][C:46](/[C:48](/[NH2:51])=[N:49]/O)=[O:47]>C(Cl)... | CCOC(=O)/C(N)=N/O | CCC(C(=O)O)(c1ccc(Cl)cc1)n1ncc2c(NC(=O)OC(C)(C)C)cccc21 | null | O=C(n1ccnc1)n1ccnc1 | 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 | 25 | 7.5 | To a suspension of 2-(4-((tert-butoxycarbonyl)amino)-1H-indazol-1-yl)-2-(4-chlorophenyl)butanoic acid from Step A above (0.16 g, 0.37 mmol) in DCM (1.5 mL) was added 1,1′-carbonyldiimdazole (0.13 g, 0.78 mmol) to give a clear solution. The mixture was stirred for 7.5 hours at RT followed by addition of ethyl 2-oximinoo... | CCOC(=O)C(N)=NOC(=O)C(CC)(c1ccc(Cl)cc1)n1ncc2c(NC(=O)OC(C)(C)C)cccc21 | null | null | null |
723,585 | ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | null | 2006-01-01T00:08:00 | true | Br[C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[C:3]=1[O:17][CH:18]([CH3:20])[CH3:19].[Li]CCCC.ClN1C(=O)CCC1=O>COCCOC.CO>[CH:18]([O:17][C:3]1[C:4]2[S:8][C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])=[N:6][C:5]=2[CH:15]=[CH:16][CH:2]=1)([CH3:20])[CH3:19] | CCNC(=O)Nc1nc2ccc(Br)c(OC(C)C)c2s1 | null | null | O=C1CCC(=O)N1Cl | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | COCCOC | null | null | null | null | null | null | null | null | null | 0 | 0.33 | A solution of 1-(6-bromo-7-isopropoxy-2-benzothiazolyl)-3-ethylurea (0.036 g, 0.10 mmol) in 0.5 mL DME was cooled down to about −78° C., and was treated with a solution of 1.6 M n-BuLi in hexanes (0.16 mL, 0.26 mmol, 2.6 eq). It was stirred at the temperature for about 20 min, then a solution of N-chlorosuccinimide (NC... | CCNC(=O)Nc1nc2cccc(OC(C)C)c2s1 | null | 25.1 | null |
1,013,831 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [OH:1][CH:2]([C:4]1[O:8][N:7]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=1)[CH3:3]>O1CCOCC1.[O-2].[O-2].[Mn+4]>[C:2]([C:4]1[O:8][N:7]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=1)(=[O:1])[CH3:3] | CCOC(=O)c1cc(C(C)O)on1 | null | null | [Mn+4] | [O-2] | 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 | null | 4.06 g of ethyl 5-(1-hydroxyethyl)-isoxazole-3-carboxylate was dissolved in 100 ml of 1,4-dioxane, and 15.20 g of manganese dioxide was then added. The mixture was stirred and heated under reflux for 5 hours. The reaction mixture was cooled to room temperature and then filtered through Celite®. The filtrate was concent... | CCOC(=O)c1cc(C(C)=O)on1 | null | 88.9 | null |
386,490 | ord_dataset-d330662edaed408d950898172aba7a4c | null | 1997-01-01T00:12:00 | true | [C@@H:1]1([C:9]([O:11]CC)=[O:10])[CH2:3][C@@H:2]1[C:4]([O:6]CC)=[O:5].[OH-].[Na+].C(O)C.Cl>O>[C@@H:1]1([C:9]([OH:11])=[O:10])[CH2:3][C@@H:2]1[C:4]([OH:6])=[O:5] | CCOC(=O)[C@H]1C[C@H]1C(=O)OCC | null | null | Cl | [Na+] | [OH-] | 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 | 25 | 8 | A stirred mixture of diethyl cis-1,2-cyclopropanedicarboxylate (53.0 g, 284.6 mmol) and sodium hydroxide (32.4 g, 809.1 mmol) in water (200 mL) was heated at reflux for 5 h. The mixture was then allowed to stir at room temperature overnight. The ethanol formed was evaporated under reduced pressure and the remaining aqu... | O=C(O)[C@H]1C[C@H]1C(=O)O | null | 95.9 | null |
1,096,677 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([O:20][CH2:21][C:22]([O:24]C)=[O:23])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([O:20][CH2:21][C:22]([OH:24])=[O:23])[C:12]1[CH:17]=[CH:16... | COC(=O)COC1(c2ccccc2OC)C(=O)Nc2ccc(Cl)cc21 | null | null | [Na+] | [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 | 13 | To a suspension of 8.00 g of the compound obtained in Step 53-1 in MeOH (400 ml) was added an aqueous solution of 1.3 mol/L NaOH, and the reaction mixture was stirred at room temperature for 13 hours. The reaction solution was concentrated, under ice cooling, 3 mol/L hydrochloric acid was added until it became acidic. ... | COc1ccccc1C1(OCC(=O)O)C(=O)Nc2ccc(Cl)cc21 | null | 95.1 | null |
339,658 | ord_dataset-4706e7a7f3cd421bb42b7f877cff8af9 | null | 1996-01-01T00:09:00 | true | [NH2:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[NH:5][C:4]([CH3:11])([CH3:10])[CH2:3]1.[C:12]([OH:17])(=O)[C:13]([CH3:15])=[CH2:14]>>[CH3:14][CH:13]([CH2:15][NH:1][CH:2]1[CH2:3][C:4]([CH3:11])([CH3:10])[NH:5][C:6]([CH3:9])([CH3:8])[CH2:7]1)[C:12]([NH:1][CH:2]1[CH2:3][C:4]([CH3:11])([CH3:10])[NH:5][C:6]([CH3:9])([CH3:8])[C... | C=C(C)C(=O)O | CC1(C)CC(N)CC(C)(C)N1 | 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 | 145 | null | Into a 3 liter flask, 1560 g of 4-amino-2,2,6,6-tetramethylpiperidine was placed. After the temperature was raised to 145° C., 430 g of methacrylic acid was added dropwise thereto. The inner temperature rose gradually and then the reaction mixture was kept at 170°±5° C., while collecting water distilled off, until the ... | CC(CNC1CC(C)(C)NC(C)(C)C1)C(=O)NC1CC(C)(C)NC(C)(C)C1 | null | 55.4 | null |
788,064 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | [CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:23][CH2:22][C:21]([C:29]([NH:31][C:32]4[CH:37]=[CH:36][C:35]([S:38][CH2:39][C:40]5[N:41]([CH2:45][CH2:46][CH2:47][CH3:48])[CH:42]=[CH:43][N:44]=5)=[CH:34][CH:33]=4)=[O:30])=[CH:20][C:19... | CCCCOCCOc1ccc(-c2ccc3c(c2)C=C(C(=O)Nc2ccc(SCc4nccn4CCCC)cc2)CCN3CC(C)C)cc1 | O=C(OO)c1cccc(Cl)c1 | null | O=S([O-])([O-])=S | [Na+] | 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 7-[4-(2-butoxyethoxy)phenyl]-N-[4-[[(1-butylimidazol-2-yl)methyl]sulfanyl]phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxamide (200 mg) in dichloromethane (10 ml) was added dropwise 70% solution of 3-chloroperbenzoic acid (108 mg) in dichloromethane (10 ml) at −78° C. To the mixture was added an ... | CCCCOCCOc1ccc(-c2ccc3c(c2)C=C(C(=O)Nc2ccc(S(=O)Cc4nccn4CCCC)cc2)CCN3CC(C)C)cc1 | null | 68.4 | null |
279,306 | ord_dataset-140fb5527ff24f97bcf0094c5d100120 | null | 1993-01-01T00:11:00 | true | [NH2:1][C:2]1[C:3]([NH:12][S:13]([CH2:16][CH3:17])(=[O:15])=[O:14])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH:18]1([C:24](Cl)=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>O1CCCC1>[CH2:16]([S:13]([NH:12][C:3]1[C:2]([NH:1][C:24]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:25])=[CH:7][C:6]([C... | CCS(=O)(=O)Nc1ncc(C(F)(F)F)cc1N | O=C(Cl)C1CCCCC1 | 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 | 1 | 2.36 g of N-(3-amino-5-trifluoromethyl-2-pyridyl)ethanesulfonamide was dissolved in 24 ml of dry tetrahydrofuran, and 1.54 g of cyclohexanecarbonyl chloride was dropwise added thereto under cooing with ice. After the dropwise addition, the mixture was stirred for one hour and further reacted at room temperature overnig... | CCS(=O)(=O)Nc1ncc(C(F)(F)F)cc1NC(=O)C1CCCCC1 | null | 88.4 | null |
1,216,981 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | C[O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]2[CH:11]=[N:12][CH:13]=[C:7]2[C:6]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:23][CH2:22]2)=[CH:17][C:16]=1[F:24])=[O:4].[OH-].[Na+].Cl>>[CH:21]1([C:18]2[CH:19]=[CH:20][C:15]([NH:14][C:6]3[C:7]4[N:8]([CH:11]=[N:12][CH:13]=4)[CH:9]=[CH:10][C:5]=3[C:3]([OH:4])=[O:2])=[C:16]([F:... | COC(=O)c1ccn2cncc2c1Nc1ccc(C2CC2)cc1F | 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 | 65 | null | A suspension of 8-(4-cyclopropyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acid methyl ester (0.28 g, 0.86 mmol) and 1M NaOH (1.03 mL, 1.03 mmol) in IMS (5 mL) was heated to 65° C. for 5 hours. The reaction mixture was then cooled to room temperature and 1M HCl was added to adjust pH to 2. The precipita... | O=C(O)c1ccn2cncc2c1Nc1ccc(C2CC2)cc1F | null | 82.2 | null |
325,143 | ord_dataset-fc4cd2699fc04ecbb7c7c831849e6b22 | null | 1996-01-01T00:02:00 | true | [CH:1](=O)/[CH:2]=[CH:3]/[CH3:4].[C:6]1(=[O:13])[CH2:11][CH2:10][CH2:9][C:8](=[O:12])[CH2:7]1>N1C=CC=CC=1>[CH3:4][CH:3]1[CH:2]=[CH:1][C:7]2[C:6](=[O:13])[CH2:11][CH2:10][CH2:9][C:8]=2[O:12]1 | O=C1CCCC(=O)C1 | C/C=C/C=O | 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 | 25 | null | A solution of crotonaldehyde (72.74 g, 1.04 mol) in 500 mL of pyridine was added to 1,3-cyclohexanedione (100 g, 0.892 mol) in 500 mL of pyridine and the mixture was heated to reflux under a nitrogen atmosphere for 1 hour. The mixture was cooled to room temperature and then filtered through magnesium sulfate (328 g). T... | CC1C=CC2=C(CCCC2=O)O1 | null | 33 | null |
1,184,676 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[NH:14][CH:15]([CH3:26])[CH2:16][C:17]([CH3:25])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])=[CH:4][CH:3]=1.[CH2:27]([O:29][C:30]([C:32]1([C:35]2[CH:40]=[CH:39][C:38](B3OC(C)(C)C(C)(C)O3)=[CH:37][CH:36]=2)[CH2:34][CH2:33]1)=[O:31])[CH3:28... | CCOC(=O)C1(c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)CC1 | Cc1noc(-c2ccc(Br)cc2)c1NC(C)CC(C)(C)c1ccccc1 | 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 procedure described in Example 2, using [5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-(1,3-dimethyl-3-phenyl-butyl)-amine and 1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester. | CCOC(=O)C1(c2ccc(-c3ccc(-c4onc(C)c4NC(C)CC(C)(C)c4ccccc4)cc3)cc2)CC1 | null | null | null |
1,303,530 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([P:12]2(=[O:28])[CH2:17][CH2:16][C:15](C(OCC)=O)([C:18]([O:20]CC)=[O:19])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[OH-].[Li+].O.Cl>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([P:12]2(=[O:28])[CH2:13][CH2:14][CH:15]([C:18]([OH:20])=[O:19])[CH2:16][CH2:17]2)[CH:6]=[CH:7][C:8]... | CCOC(=O)C1(C(=O)OCC)CCP(=O)(c2ccc([N+](=O)[O-])c(OC)c2)CC1 | 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 | 75 | 4 | Diethyl 1-(3-methoxy-4-nitrophenyl)phosphinane-4,4-dicarboxylate 1-oxide (INTERMEDIATE 59) (4.5 g, 10.89 mmol) and lithium hydroxide (1.043 g, 43.55 mmol) were added to a 200-mL round bottomed flask. Water (30 mL) and THF (30 mL) were added to give a brown suspension. The mixture was heated to 75° C. and stirred at tha... | COc1cc(P2(=O)CCC(C(=O)O)CC2)ccc1[N+](=O)[O-] | null | 11.7 | null |
1,258,916 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | [C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[CH:8][C:7]([CH2:17][CH2:18][CH:19]=O)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:21][C:22]1[CH:23]=[C:24]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:25]=[CH:26][C:27]=1[CH3:28].CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[C:1]([N:... | Cc1ccc(-c2cc(CCC=O)nn2C(C)(C)C)cc1 | Cc1ccc(N2CCNCC2)cc1C | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | null | 89 mg (84%) of target compound was obtained by using a method same as in Example 1 by using 3-(1-tert-butyl-5-p-tolyl-1H-pyrazol-3-yl)propanal (60 mg, 0.222 mmol), 1-(3,4-dimethylphenyl)piperazine (42 mg, 0.222 mmol), DIPEA (0.06 mL, 0.333 mmol) and NaBH(OAc)3 (141 mg, 0.666 mmol). | Cc1ccc(-c2cc(CCCN3CCN(c4ccc(C)c(C)c4)CC3)nn2C(C)(C)C)cc1 | null | null | null |
1,758,614 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[C:10]([NH2:12])[CH:9]=[N:8]2)[CH:2]=1.[F:13][C:14]([F:22])([F:21])[CH2:15][CH:16]([CH3:20])[C:17](O)=[O:18].Cl.CN(C)CCCN=C=NCC>ClC(Cl)C>[F:13][C:14]([F:22])([F:21])[CH2:15][CH:16]([CH3:20])[C:17]([NH:12][C:10]1[CH:9]=[N:8][N:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH:1... | CC(CC(F)(F)F)C(=O)O | Nc1cnn(-c2cccnc2)c1 | null | CCN=C=NCCCN(C)C | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of 1-(pyridin-3-yl)-1H-pyrazol-4-amine (0.150 g, 0.93 mmol) in dichloroethane (1.8 ml) was added 4,4,4-trifluoro-2-methylbutanoic acid (0.14 g, 0.93 mmol) and 4-N,N-dimethylaminopyridine (0.23 g, 1.87 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.36 g, 1.87 mmol). The re... | CC(CC(F)(F)F)C(=O)Nc1cnn(-c2cccnc2)c1 | null | 54.1 | null |
1,289,824 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [N:1]1[N:2]2[CH:10]=[CH:9][CH:8]=[C:3]2[C:4]([NH2:7])=[N:5][CH:6]=1.[Br:11]N1C(C)(C)C(=O)N(Br)C1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[Br:11][C:8]1[CH:9]=[CH:10][N:2]2[C:3]=1[C:4]([NH2:7])=[N:5][CH:6]=[N:1]2 | CC1(C)C(=O)N(Br)C(=O)N1Br | Nc1ncnn2cccc12 | null | O=S([O-])([O-])=S | [Na+] | 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 | 4 | A suspension of pyrrolo[2,1-f][1,2,4]triazin-4-amine (0.5 g, 0.004 mol) in dichloromethane (100 mL) was stirred and cooled between −10° C. and −14° C. under nitrogen atmosphere. A solution of 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (544 mg, 0.002 mol) in dichloromethane (100 mL) added dropwise over a 1 h. After... | Nc1ncnn2ccc(Br)c12 | null | null | null |
692,396 | ord_dataset-35824232b132464aa99e71aba765981d | null | 2005-01-01T00:12:00 | true | [C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH2:18]N(C(OC)=O)C[CH2:15]3)[CH2:7]1)(=[O:3])[CH3:2].[CH3:26][O:27]C1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1>>[CH2:15]1[C:14]2[CH:13]=[C:12]([N:8]3[CH2:7][C@H:6]([CH2:5][NH:4][C:1](=[O:3])[CH3:2])[O:10][C:9]3=[O:11]... | COC(=O)N1CCc2cc(N3C[C@H](CNC(C)=O)OC3=O)ccc2C1 | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)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 | Following the general procedure of Example 5, and making non-critical variations but substituting (−)-N-[[(5S)-3-(3,4-dihydro-1H-2-benzopyran-7-yl)-2-oxo-5-oxazolidinyl]methyl]acetamide (Step 4) for methyl 6-[(5S)-5-[(acetylamino)methyl]-2-oxo-3-oxazolidinyl]-3,4-dihydro-2(1H)-isoquinolinecarboxylate, using 0.7 mol-equ... | CC(=O)NC[C@H]1CN(c2ccc3c(c2)COCC3)C(=O)O1 | null | null | null |
468,973 | ord_dataset-f1b9e9741a6a4cc68e7070df811f86bb | null | 2000-01-01T00:07:00 | true | [Cl-].[CH3:2][C:3]1[CH:4]=[C:5]([C:14]([N:16]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][N:25]([C:34]([C:36]3[CH:41]=[C:40]([CH3:42])[C:39]([O:43]C(=O)C)=[C:38]([CH3:47])[CH:37]=3)=[O:35])[CH2:24][CH2:23][O:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[O:15])[CH:6]=[C:7]([CH3:13])[C:8]=1[O:9]C(=O)C.C[O... | CC(=O)Oc1c(C)cc(C(=O)N2CCOCCOCCN(C(=O)c3cc(C)c(OC(C)=O)c(C)c3)CCOCCOCC2)cc1C | null | null | C[O-] | [Cl-] | [Na+] | 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 | 0 | 2 | To 40 ml of mixed solvent of anhydrous methanolmethylene chloride was dissolved 0.5 g/0.8 mmol of 1,10-bis(3',5'-dimethyl-4'-acetoxyphenylcarbonyl)-1,10-diaza-4,7,13,16-tetraoxacyclooctadecane, and the solution was cooled to 0° C. To this solution was added 2.6 ml of freshly prepared 1M methanol solution of sodium meth... | Cc1cc(C(=O)N2CCOCCOCCN(C(=O)c3cc(C)c(O)c(C)c3)CCOCCOCC2)cc(C)c1O | null | 89.5 | null |
449,885 | ord_dataset-a4f0b79f6b9847168861270b79f84afa | null | 1999-01-01T00:11:00 | true | [C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([C:19](=[O:40])[CH2:20][N:21]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[C:23]([C:30]([O:32]CC5C=CC=CC=5)=[O:31])=[CH:22]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.[OH-].[OH-].[Pd+2]>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O... | CC(C)(C)c1csc(-c2cc3cc(C(=O)Cn4cc(C(=O)OCc5ccccc5)c5ccccc54)ccc3o2)n1 | null | null | [Pd+2] | [OH-] | 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 | A solution of benzyl 1-{2-[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]-2-oxoethyl}indole-3-carboxylate (140 mg) in tetrahydrofuran (4 ml) was hydrogenated over 10% Pd(OH)2 (22 mg) at room temperature under atmospheric pressure. After removal of the catalyst by filtration the filtrate was concentrated under reduced pre... | CC(C)(C)c1csc(-c2cc3cc(C(=O)Cn4cc(C(=O)O)c5ccccc54)ccc3o2)n1 | null | 76.9 | null |
697,190 | ord_dataset-4e9c2fa02a7544fd839206719263345f | null | 2006-01-01T00:02:00 | true | [C:1]([CH:4]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]([O:7]CC)=O)(=O)[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:28]1([CH3:43])[CH:33]=[C:32]([CH3:34])[CH:31]=[C:30]([CH3:35])[C:29]=1[C:36]1[C:37]([CH3:42])=[N:38][NH:39][C:40]=1[NH2:41]>C1(C)C(C)=CC=CC=1>[C:28]1([CH3:43])[CH:33]=[C:32]([CH3:34])[CH:31]=[C:30]([C... | Cc1cc(C)c(-c2c(C)n[nH]c2N)c(C)c1 | CCOC(=O)CC(C(C)=O)C(=O)OCC | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | Cc1ccccc1C | null | null | null | null | null | null | null | null | null | null | 3 | Diethyl acetylsuccinate (0.3 mL) and a catalytic amount of 4-toluenesulfonic acid monohydrate were added to a solution of 4-mesityl-3-methyl-1H-5-pyrazoleamine (100 mg) of Reference Example 1 in xylene (5 mL). Under heating under reflux, the mixture was stirred for three hours while distilling water off with Dean-Stark... | CCOC(=O)Cc1c(C)[nH]c2c(-c3c(C)cc(C)cc3C)c(C)nn2c1=O | null | null | null |
654,471 | ord_dataset-fe016e2f90e741a590ad77fd5933161f | null | 2004-01-01T00:11:00 | true | [N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1[S:11][C:10]([CH:12]=O)=[CH:9][CH:8]=1.N1(C2C=C[C:22]([CH:23]=[O:24])=CC=2)C=CC=N1>>[N:3]1[CH:4]=[CH:5][CH:6]=[N:1][C:2]=1[C:7]1[S:11][C:10](/[CH:12]=[CH:22]/[CH:23]=[O:24])=[CH:9][CH:8]=1 | O=Cc1ccc(-c2ncccn2)s1 | O=Cc1ccc(-n2cccn2)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 was prepared by a procedure analogous to Reference Example 30 by substituting 5-(2-pyrimidinyl)-2-thiophenecarboxaldehyde (prepared as described in Reference Example 86) for the 4-(1H-pyrazol-1-yl)-benzaldehyde of Reference Example 30. MS 217 (M+H)+. | O=C/C=C/c1ccc(-c2ncccn2)s1 | null | null | null |
824,386 | ord_dataset-0ca5627a13c049a99463095023b09fe5 | null | 2008-01-01T00:06:00 | true | [CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[N:9]=[CH:10][C:11]([C:14]#[N:15])=[N:12][CH:13]=2)=[CH:5][CH:4]=1)=[O:2].C([O-])([O-])=[O:19].[K+].[K+].OO>CS(C)=O.C(Cl)Cl>[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[N:9]=[CH:10][C:11]([C:14]([NH2:15])=[O:19])=[N:12][CH:13]=2)=[CH:5][CH:4]=1)=[O:2] | N#Cc1cnc(Oc2ccc(C=O)cc2)cn1 | O=C([O-])[O-] | null | OO | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 22 | Dissolve 5-(4-formylphenoxy)pyrazine-2-carbonitrile (1.87 g, 8.30 mmol) and K2CO3 (0.573 g, 4.15 mmol) in DMSO (21 mL). Add 30% H2O2 (2.4 mL, 20.8 mmol) and stir at room temperature for 22 hours. Add additional K2CO3 (0.573 g, 4.15 mmol) and heat at 55° C for about 2.5 hours. Cool the reaction mixture and dilute with C... | NC(=O)c1cnc(Oc2ccc(C=O)cc2)cn1 | null | 47.4 | null |
908,312 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | C([Li])CCC.[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)#[CH:7].[C:14](=[O:16])=[O:15]>C1COCC1>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:6]#[C:7][C:14]([OH:16])=[O:15] | O=C=O | C#Cc1ccccn1 | null | [Li]CCCC | 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 | 0.5 | 6.3 mL of n-butyllithium solution (1.6M in hexane) is added dropwise at −10° C. to a solution of 1 g (9.7 mmol) of 2-ethynylpyridine in 30 mL of absolute THF and stirred for 30 minutes. At −78° C., dry ice is added batchwise and the reaction mixture is allowed to heat up to ambient temperature. After about 1 hour, the ... | O=C(O)C#Cc1ccccn1 | null | null | null |
95,248 | ord_dataset-6f715747ea754945a2f0af4a8482c7d2 | null | 1982-01-01T00:06:00 | true | Br.Br.[N:3]1([C:9]2[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.O.C(=O)([O-])O.[Na+].[C:22](OC(=O)C)(=[O:24])[CH3:23]>ClC(Cl)Cl>[C:22]([N:6]1[CH2:5][CH2:4][N:3]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=2)[CH2:8][CH2:7]1)(=[O:24])[CH3:23] | Oc1cccc(N2CCNCC2)c1 | CC(=O)OC(C)=O | null | Br | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | 10 | 3 | To a stirred solution of 80 parts of 3-(1-piperazinyl)phenol dihydrobromide in 360 parts of water and 180 parts of trichloromethane are added portionwise 42 parts of sodium hydrogen carbonate at 10° C. Then there are added dropwise, during a 15 minutes-period, 26 parts of acetic acid anhydride while cooling at 10° C. U... | CC(=O)N1CCN(c2cccc(O)c2)CC1 | null | 70 | null |
823,003 | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | null | 2008-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[N:14]=[CH:15][C:16]([C:17]([OH:19])=O)=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.[NH2:20][C:21]1[CH:22]=[C:23]([S:27]([NH2:30])(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1>>[S:27]([C:23]1[CH:22]=[C:21]([NH:20][C:17]([C:16]2[CH:15]=[N:14][N:11]3[CH:12]=[CH:13][C:8]([C:5]4[CH... | O=C(O)c1cnn2ccc(-c3ccc(Cl)cc3)nc12 | Nc1cccc(S(N)(=O)=O)c1 | 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 5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.22) and 3-amino-benzenesulfonamide according to general procedure II. Pale-yellow solid. MS (ISP) 428.3 [(M+H)+]; mp 345° C. | NS(=O)(=O)c1cccc(NC(=O)c2cnn3ccc(-c4ccc(Cl)cc4)nc23)c1 | null | null | null |
1,411,912 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[C:10]([C:12]3[N:17]=[C:16]([C:18](=S)[NH2:19])[CH:15]=[CH:14][CH:13]=3)[CH:9]=[N:8]2)[CH:2]=1.[NH2:21][OH:22]>O1CCOCC1.C1COCC1>[OH:22][NH:21][C:18]([C:16]1[CH:15]=[CH:14][CH:13]=[C:12]([C:10]2[CH:9]=[N:8][N:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:11]=2)[N:17]=1)=[NH... | NO | NC(=S)c1cccc(-c2cnn(-c3cccnc3)c2)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | C1COCCO1 | null | null | null | null | null | null | null | null | null | 60 | 1 | With heating, 0.4 g (1.4 mmol) of 6-(1-pyridin-3-yl-1H-pyrazol-4-yl)pyridine-2-carbothioamide were dissolved in 40 ml of dioxane-THF 1:3, 0.4 ml of hydroxylamine (50% strength aqueous solution, corresponds to 6.8 mmol) was added and the mixture was stirred at 60° C. for 1 h and then concentrated by evaporation. The cru... | N=C(NO)c1cccc(-c2cnn(-c3cccnc3)c2)n1 | null | null | null |
1,365,271 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[O:19])=[CH:14][CH:13]=2)[N:3]=1.C1C(=O)N([Br:33])C(=O)C1.OS([O-])=O.[Na+]>C(#N)C.C(OCC)(=O)C>[Br:33][C:10]1[C:2]([Cl:1])=[N:3][C:4]([NH:11][C:12]2[CH:13]=[CH:14][C:15](... | NC(=O)c1ccc(Cl)nc1Nc1ccc(C(=O)N2CCOCC2)cc1 | O=C1CCC(=O)N1Br | null | O=S([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 8 | A suspension of 6-chloro-2-(4-(morpholine-4-carbonyl)phenylamino)nicotinamide (500 mg, 1.385 mmol) and NBS (250 mg, 1.4 mmol) in acetonitrile (10 mL) was stirred at overnight. The reaction mixture was treated with 1M NaHSO3 and stirred at rt for 2 h. Next, the reaction mixture was diluted with ethyl acetate and the pre... | NC(=O)c1cc(Br)c(Cl)nc1Nc1ccc(C(=O)N2CCOCC2)cc1 | null | 38.6 | null |
762,482 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | Cl[C:2]1[C:7]([C:8](OCC)=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=1.[CH:14]1([NH2:17])[CH2:16][CH2:15]1>>[CH:14]1([NH:17][C:2]2[C:7]([CH:8]=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=2)[CH2:16][CH2:15]1 | CCOC(=S)c1cnc(C)nc1Cl | NC1CC1 | 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 | 4-cyclopropylamino-2-methylthiopyrimidine-5-carboxaldehyde was prepared as described in Example 1 (steps A through C) starting with ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate (Aldrich Chemical Co.) and cyclopropyl amine (Aldrich Chemical Co.). | Cc1ncc(C=S)c(NC2CC2)n1 | null | null | null |
365,544 | ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | null | 1997-01-01T00:05:00 | true | [O:1]([C:8]1[CH:21]=[CH:20][C:11]([CH2:12][NH:13][C:14]([CH:16]2[CH2:19][CH2:18][CH2:17]2)=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:16]1([CH2:14][NH:13][CH2:12][C:11]2[CH:20]=[CH:21][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:9][CH:10]=2)[CH2:... | O=C(NCc1ccc(Oc2ccccc2)cc1)C1CCC1 | null | null | [Al+3] | [H-] | [Li+] | 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 | 0 | null | A cooled (0° C.) solution of N-(4-phenoxybenzyl)cyclobutanecarboxamide (0.60 g, 2.1 mmol) in THF (7 mL) was treated with 1M solution of LAH in THF (2.1 mL). The solution was refluxed for 2 hours then cooled to 0° C. and quenched with Na2SO4 ·10 H2O. The suspension was diluted with THF and filtered through a pad of celi... | c1ccc(Oc2ccc(CNCC3CCC3)cc2)cc1 | null | 99.7 | null |
1,670,859 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].C=O.[C:14]1(B(O)O)C=CC=CC=1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5](=[CH2:14])[C:6]2=[O:11] | O=C1CCc2c(F)cccc21 | OB(O)c1ccccc1 | null | C=O | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 25 | null | To a 1000 mL round bottle flask were charged 4-fluoro-2,3-dihydro-1H-inden-1-one (249a) (5.04 g, 33.6 mmol), paraformaldehyde (10.08 g, 336 mmol), phenylboronic acid (4.92 g, 40.3 mmol) followed by toluene (235 mL), to the suspension was added TFA 2.6 mL, 33.6 mmol), and the resulting suspension was refluxed for 4 hrs,... | C=C1Cc2c(F)cccc2C1=O | null | 71.8 | null |
399,487 | ord_dataset-7fed188163cf4ccca934ec71504c7f8a | null | 1998-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].[S:23]1[CH2:29][C:27](=[O:28])[NH:26][C:24]1=[S:25]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[C:29]3[S:23][C:24](=[S:25])[NH:26][C:27]3=... | O=C1CSC(=S)N1 | O=Cc1ccc(OCc2ccc(Cl)cc2)cc1 | null | CC(=O)[O-] | [Na+] | 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 | Under a nitrogen atmosphere in a round bottom flask 4-[(4-chlorophenyl)methoxy]benzaldehyde (0.40 g, 1.62 mmol) was dissolved in acetic acid (8.1 ml) while stirring. To this solution was added sodium acetate (0.47 g, 5.7 mmol) followed by the addition of rhodanine (0.22 g, 1.65 mmol). The reaction mixture was heated to... | O=C1NC(=S)SC1=Cc1ccc(OCc2ccc(Cl)cc2)cc1 | null | null | null |
1,580,592 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:8]=[CH:7]2)([O-])=O>CO.O=[Pt]=O>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:8]=[CH:7]2 | COC(=O)Cn1ccc2cc([N+](=O)[O-])ccc21 | null | null | O=[Pt]=O | 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 | To a solution of methyl 2-(5-nitro-1H-indol-1-yl)acetate (830 mg, 3.54 mmol) in MeOH (50 ml), a catalytic amount of PtO2 was added, and the mixture was reacted under H2 atmosphere in a Parr apparatus at 30 psi for 15 minutes. The catalyst was filtered off, the solvent was removed and crude methyl 2-(5-amino-1H-indol-1-... | COC(=O)Cn1ccc2cc(N)ccc21 | null | null | null |
591,907 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | C([Li])CCC.C(P([CH2:12][S:13]([O:16][CH2:17][CH3:18])(=[O:15])=[O:14])(CC)=O)C.[CH3:19][C:20]1[S:24][C:23]([CH:25]=O)=[CH:22][CH:21]=1>C1COCC1>[CH3:25][C:23]1[S:24][C:20]([CH:19]=[CH:12][S:13]([O:16][CH2:17][CH3:18])(=[O:14])=[O:15])=[CH:21][CH:22]=1 | CCOS(=O)(=O)CP(=O)(CC)CC | Cc1ccc(C=O)s1 | null | [Li]CCCC | 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 | 0.33 | n-Butyl lithium (1.6 mL of a 2.5 M solution in hexanes, 4.0 mmol) was added dropwise to a solution of ethyl diethylphosphorylmethanesulfonate (1.0 g, 3.8 mmol), prepared as described in Tetrahedron, 1987, 43(21), 5125, at −78° C. in THF (15 mL). The mixture was stirred for 20 min. then 5-methyl-2-thiophenecarboxaldehyd... | CCOS(=O)(=O)C=Cc1ccc(C)s1 | null | null | null |
1,600,259 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([C@:8]2([CH3:19])[CH2:13][C@@H:12]([C:14]([F:17])([F:16])[F:15])[O:11][C:10]([NH2:18])=[N:9]2)[CH:7]=1.[F:21][CH:22]([F:32])[C:23]1[CH:24]=[CH:25][C:26]([C:29](O)=[O:30])=[N:27][CH:28]=1>>[NH2:18][C:10]1[O:11][C@H:12]([C:14]([F:16])([F:17])[F:15])[CH2:13][C@:8]([C:6]2[CH:7]... | C[C@@]1(c2cc(N)ccc2F)C[C@@H](C(F)(F)F)OC(N)=N1 | O=C(O)c1ccc(C(F)F)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 coupling of (4S,6S)-4-(5-amino-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (XI-1) and 5-(difluoromethyl)picolinic acid [J. D. Scott et al. WO2011044181 (2011)] following General Procedure G yielded the title compound as a colorless amorphous solid. MS: m/z=447.5 [M+H]+. | C[C@@]1(c2cc(NC(=O)c3ccc(C(F)F)cn3)ccc2F)C[C@@H](C(F)(F)F)OC(N)=N1 | null | null | null |
589,719 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | [C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[C:12]([N:14]([CH3:16])[CH3:15])[C:11]([C:17]([F:20])([F:19])[F:18])=[CH:10][C:9]=1[NH2:21])([CH3:4])([CH3:3])[CH3:2].C([O:27][C:28](=O)[CH2:29][C:30](=[O:50])[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([N:37]2[C:41]([CH2:42][O:43][CH:44]3[CH2:49][CH2:48][CH2:47][CH2:46][O:45]3)=[C... | CC(C)(C)OC(=O)CC(=O)c1cccc(-n2nncc2COC2CCCCO2)c1 | CN(C)c1cc(NC(=O)OC(C)(C)C)c(N)cc1C(F)(F)F | 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 (2-amino-5-dimethylamino-4-trifluoromethyl-phenyl)-carbamic acid tert.-butyl ester (Example J6) (160 mg, 0.5 mmol) and (RS)-3-oxo-3-{3-[5-(tetrahydro-pyran-2-yloxymethyl)-[1,2,3]triazol-1-yl]-phenyl}-propionic acid tert-butyl ester (Example K5) (201 mg, 0.5 mmol) according to the ge... | CN(C)c1cc(NC(=O)OC(C)(C)C)c(NC(=O)CC(=O)c2cccc(-n3nncc3COC3CCCCO3)c2)cc1C(F)(F)F | null | null | null |
359,540 | ord_dataset-58ec5adfcd8648dc9e26ee757d289517 | null | 1997-01-01T00:03:00 | true | Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[CH3:9][O:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:9][O:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=2)[CH:13]=1 | COC(=O)c1cccc(O)c1 | Brc1cccc(Br)n1 | null | O=C([O-])[O-] | [Cs+] | 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 | 120 | 3 | A solution of 2.37 g of 2,6-dibromopyridine and 1.52 g of 3-hydroxybenzoic acid methyl ester in 10 ml of dimethylformamide is mixed with 6.6 g of cesium carbonate and heated to 120° C. with stirring for 3 hours. The reaction mixture is filtered on diatomaceous earth, rewashed with dichloromethane and the filtrate is co... | COC(=O)c1cccc(Oc2cccc(Br)n2)c1 | null | 96.8 | null |
23,735 | ord_dataset-fcf7c02bbb814fe696760b5fbfee16bb | null | 1977-01-01T00:05:00 | true | [CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]2[N:13]=[CH:14][CH:15]=[CH:16][C:4]=2[C:3]1=[O:17].[H-].[Na+].[CH3:20][N:21]([CH3:36])[CH2:22][CH2:23][CH2:24]OS(C1C=CC(C)=CC=1)(=O)=O>C1(C)C(C)=CC=CC=1>[CH3:20][N:21]([CH3:36])[CH2:22][CH2:23][CH2:24][N:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:2]... | CN1C(=O)c2cccnc2Nc2ccccc21 | Cc1ccc(S(=O)(=O)OCCCN(C)C)cc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1C | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 4.5 gm of 6,11-dihydro-6-methyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one, 0.83 gm of 55% sodium hydride in mineral oil, and 100 ml of absolute xylene was refluxed for two hours. Thereafter, 7 gm of p-toluenesulfonic acid 3-dimethylamino-n-propyl ester were added, and the resulting mixture was refluxed for ... | CN(C)CCCN1c2ccccc2N(C)C(=O)c2cccnc21 | null | 38.7 | null |
414,469 | ord_dataset-275344fd078b4340b89ca0b6e92beb95 | null | 1998-01-01T00:10:00 | true | [OH:1][C@@H:2]1[C@H:11]2[C:6]([CH:7]=[CH:8][C@H:9]([CH3:29])[C@@H:10]2[CH2:12][CH2:13][C@H:14]2[O:19][C:18](=[O:20])[CH2:17][C@H:16]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:15]2)=[CH:5][CH2:4][CH2:3]1.[CH2:30]([C:32]([CH3:38])([CH2:36][CH3:37])[C:33](Cl)=[O:34])[CH3:31]>>[CH2:30]([C:32]... | CCC(C)(CC)C(=O)Cl | C[C@H]1C=CC2=CCC[C@H](O)[C@@H]2[C@H]1CC[C@@H]1C[C@@H](O[Si](C)(C)C(C)(C)C)CC(=O)O1 | 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 | A procedure similar to that described in Example 4, above, was followed, but using 1.0 g (2.4 mmol) of (4R,6R)-6-{2-[(1S,2S,8S,8aR)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described in Japanese Patent Kokai Application No. Sho 59-175450... | CCC(C)(CC)C(=O)O[C@H]1CCC=C2C=C[C@H](C)[C@H](CC[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)CC(=O)O3)[C@H]21 | null | 74.4 | null |
1,286,986 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [NH:1]([C:3]1[N:4]=[C:5]2[CH:11]=[CH:10][N:9]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]2=[N:7][CH:8]=1)[NH2:2].[C:22]([O:26][C:27]([N:29]1[CH2:33][C@H:32]([CH2:34][CH3:35])[C@H:31]([C:36](O)=[O:37])[CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C... | Cc1ccc(S(=O)(=O)n2ccc3nc(NN)cnc32)cc1 | CC[C@H]1CN(C(=O)OC(C)(C)C)C[C@H]1C(=O)O | 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 | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 2 | To a suspension of 2-hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (5.00 g, 16.48 mmol, Example 1, Step D) and (cis)-1-(tert-butoxycarbonyl)-4-ethylpyrrolidine-3-carboxylic acid (4.01 g, 16.48 mmol) in DCM (70 mL) were added TEA (5.75 mL, 41.2 mmol) and HATU (6.90 g, 18.15 mmol, Novabiochem). The resulting suspension wa... | CC[C@@H]1CN(C(=O)OC(C)(C)C)C[C@@H]1C(=O)NNc1cnc2c(ccn2S(=O)(=O)c2ccc(C)cc2)n1 | null | null | null |
1,557,572 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.Br[CH2:9][C:10]1[S:14][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:12][CH:11]=1>CN(C=O)C>[N:3]1([CH2:9][C:10]2[S:14][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:12][CH:11]=2)[CH:7]=[CH:6][N:5]=[CH:4]1 | CCOC(=O)c1ncc(CBr)s1 | c1c[nH]cn1 | 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 | 0.75 | To a cooled (0 C) suspension of sodium hydride (60% in oil, 82 mg, 2.05 mmol) in dry DMF (2 ml) was added imidazole (93 mg, 1.37 mmol) as a solution in dry DMF (0.5 ml). Mixture was stirred at RT 45 min, cooled to 0° C. followed by addition of ethyl 5-(bromomethyl)thiazole-2-carboxylate (342 mg, 1.37 mmol) dissolved in... | CCOC(=O)c1ncc(Cn2ccnc2)s1 | null | 44 | null |
451,199 | ord_dataset-3bcdb559226a40d89406474c02d082d1 | null | 1999-01-01T00:12:00 | true | [I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([C:18]([N:20]([CH3:25])[CH2:21][CH2:22][CH2:23]O)=[O:19])[N:9]=1.CCN(CC)CC.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][... | CS(=O)(=O)Cl | CN(CCCO)C(=O)c1cc2ccccc2c(-c2ccccc2I)n1 | null | CN(C)c1ccncc1 | 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 | null | To a solution of 1-(2-iodophenyl)-N-methyl-N-(3-hydroxypropyl)-3-isoquinolinecarbo-xamide (20 mg, 0.045 mmol), DMAP (5.5 mg, 0.045 mmol), and Et3N (0.02 mL, 0.14 mmol) in CH2Cl2 (2 mL) at 0° C. was added dropwise MsCl (0.006 mL, 0.77 mmol). The resulting mixture was stirred at 0° C. and monitored by TLC. After stirring... | CN(CCCS(C)(=O)=O)C(=O)c1cc2ccccc2c(-c2ccccc2I)n1 | null | 69.9 | null |
1,420,651 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | O.[C:2]1(C)C=CC(S(O)(=O)=O)=CC=1.[F:13][C:14]([F:22])([C:18]([OH:21])([CH3:20])[CH3:19])[C:15]([OH:17])=[O:16].C(=O)([O-])O.[Na+]>CO>[F:13][C:14]([F:22])([C:18]([OH:21])([CH3:20])[CH3:19])[C:15]([O:17][CH3:2])=[O:16] | CC(C)(O)C(F)(F)C(=O)O | Cc1ccc(S(=O)(=O)O)cc1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | null | null | A catalytic amount of p-toluenesulfonic acid monohydrate was added to a mixture of 73.3 g of Intermediate 3 in Example 3 and 300 g of methanol. With stirring in a nitrogen atmosphere, the reaction mixture was heated under reflux for 12 hours. After cooling, the reaction mixture was poured into a saturated sodium hydrog... | COC(=O)C(F)(F)C(C)(C)O | null | 65 | null |
1,556,694 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][NH2:9])[CH:3]=1.[F:11][C:12]([F:19])([F:18])[C:13](=O)[CH2:14][C:15]#[N:16]>>[C:2]1([CH3:10])[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[C:15]([NH2:16])=[CH:14][C:13]([C:12]([F:19])([F:18])[F:11])=[N:9]2)[CH:3]=1 | Cc1cccc(NN)c1 | N#CCC(=O)C(F)(F)F | null | 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 | Following the procedure in Example 161A Step 3, m-tolylhydrazine hydrochloride (1.15 g, 7.30 mmol) and 4,4,4-trifluoro-3-oxobutanenitrile (1.0 g, 7.30 mmol) were reacted to give 1-m-tolyl-3-(trifluoromethyl)-1H-pyrazol-5-amine (380 mg, 1.57 mmol, 22%). 1H NMR (300 MHz, DMSO-d6) δ 7.60-7.20 (m, 4H), 5.82-5.61 (m, 3H), 2... | Cc1cccc(-n2nc(C(F)(F)F)cc2N)c1 | null | 21.5 | null |
1,059,171 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | C(OC([N:6]1[CH2:10][CH2:9][C:8]([OH:21])([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH2:7]1)=O)C.[OH-].[K+]>O1CCOCC1.C(O)CCC>[F:20][C:17]([F:18])([F:19])[C:14]1[CH:13]=[CH:12][C:11]([C:8]2([OH:21])[CH2:9][CH2:10][NH:6][CH2:7]2)=[CH:16][CH:15]=1 | CCOC(=O)N1CCC(O)(c2ccc(C(F)(F)F)cc2)C1 | null | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CCCCO | null | null | null | null | null | null | null | null | null | null | null | To a solution of 1.98 mmol rac-3-Hydroxy-3-(4-trifluoromethyl-phenyl)-pyrrolidine-1-carboxylic acid ethyl ester in 15 ml dioxane., was added 8 ml of a 2.5N solution of KOH in butanol. The solution was stirred under reflux for 2 hours. The solvent was removed in vacuo and the residue was taken in water. The aqueous phas... | OC1(c2ccc(C(F)(F)F)cc2)CCNC1 | null | 57 | null |
762,876 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | [CH3:1][C:2]1([CH3:22])[C:6]2[CH:7]=[C:8]([CH2:20][OH:21])[CH:9]=[C:10](B3OC(C)(C)C(C)(C)O3)[C:5]=2[O:4][CH2:3]1.Br[C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[O:32][C:33]([F:36])([F:35])[F:34])[CH:27]=[O:28]>>[OH:21][CH2:20][C:8]1[CH:9]=[C:10]([C:30]2[CH:29]=[C:26]([CH:25]=[CH:24][C:31]=2[O:32][C:33]([F:34])([F:35])[... | O=Cc1ccc(OC(F)(F)F)c(Br)c1 | CC1(C)COc2c(B3OC(C)(C)C(C)(C)O3)cc(CO)cc21 | 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 intermediate 3-(5-hydroxymethyl-3,3-dimethyl-2,3-dihydro-benzofuran-7-yl)-4-trifluoromethoxy-benzaldehyde was prepared in a similar manner to example 1a using [3,3-dimethyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-5-yl]-methanol and 3-bromo-4-trifluoromethoxy benzaldehyde. 59% yield. ... | CC1(C)COc2c(-c3cc(C=O)ccc3OC(F)(F)F)cc(CO)cc21 | null | 59 | null |
957,124 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [N:1]1([CH:6]2[CH2:11][CH2:10][CH:9]([NH:12]C(=O)OC(C)(C)C)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[N:1]1([CH:6]2[CH2:11][CH2:10][CH:9]([NH2:12])[CH2:8][CH2:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1 | CC(C)(C)OC(=O)NC1CCC(N2CCCC2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 25 | 3 | tert-butyl N-(4-pyrrolidin-1-ylcyclohexyl)carbamate (Intermediate 238; 222 mg, 0.83 mmol) was taken up in DCM (1.5 mL) and TFA (1 mL). The reaction mixture was stirred at ambient temperature for 3 hours, poured directly onto an SCX-3 cartridge (2 g), pre-wet with DCM. The cartridge was washed through with DCM (10 mL), ... | NC1CCC(N2CCCC2)CC1 | null | 73.7 | null |
1,203,625 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [C:1]([C:3]1[C:4]([N:11]([CH3:15])[C:12](=[O:14])[CH3:13])=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=1)#[N:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[NH2:2][C:1]1[C:3]2[CH:8]=[N:7][C:6]([S:9][CH3:10])=[N:5][C:4]=2[N:11]([CH3:15])[C:12](=[O:14])[CH:13]=1 | CSc1ncc(C#N)c(N(C)C(C)=O)n1 | null | null | C[Si](C)(C)[N-][Si](C)(C)C | [Li+] | 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 N-(5-cyano-2-methylsulfanyl-pyrimidin-4-yl)-N-methyl-acetamide (400 mg, 1.80 mmol) in THF (18 mL) was added a solution of lithium bis(trimethyl-silyl)amide (1.0 M in hexane, 7.2 mL, 7.20 mmol) at RT. The reaction mixture was stirred at RT for 1 h, then quenched with water (100 mL). The resulting mixtur... | CSc1ncc2c(N)cc(=O)n(C)c2n1 | null | 40.7 | null |
1,229,929 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH2:31][CH:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[C:14](=O)[CH2:15][CH2:16][C:17]([C:19]3[S:20][C:21]([CH:24]([OH:29])[C:25]([F:28])([F:27])[F:26])=[CH:22][N:23]=3)=O)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+:42].[OH-].[Na+]>C(O)(=O)C>[CH:... | O=C(CCC(=O)C(CC1CCOCC1)c1ccc(S(=O)(=O)C2CC2)cc1)c1ncc(C(O)C(F)(F)F)s1 | [NH4+] | null | CC(=O)[O-] | [Na+] | [OH-] | 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 | 80 | 3 | A mixture of 5-[4-(cyclopropylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)-1-[5-(2,2,2-trifluoro-1-hydroxyethyl)-1,3-thiazol-2-yl]hexane-1,4-dione (0.45 g), ammonium acetate (0.31 g) and acetic acid (6 mL) was stirred at 80° C. for 3 hr. The reaction mixture was neutralized with 8M sodium hydroxide, and extracted with... | O=S(=O)(c1ccc(C(CC2CCOCC2)c2ccc(-c3ncc(C(O)C(F)(F)F)s3)[nH]2)cc1)C1CC1 | null | 65 | null |
1,580,300 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [C:1]([N:4]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[N:5]1[CH2:10][C:9]([CH:11]=O)=[N:8][N:7]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:6]1=[O:20])(=[O:3])[CH3:2].[CH3:28][N:29]([CH3:31])[NH2:30].Cl>CCO>[C:1]([N:4]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[N:5]1[CH2:10][C... | CC(=O)N(C(=O)OC(C)(C)C)N1CC(C=O)=NN(C(=O)OC(C)(C)C)C1=O | CN(C)N | null | Cl | 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 | 25 | 20 | To a solution of tert-butyl 4-[acetyl(tert-butoxycarbonyl)amino]-6-formyl-3-oxo-5H-1,2,4-triazine-2-carboxylate (461 mg, 1.20 mmol) in EtOH was added N,N-dimethylhydrazine (0.110 mL, 1.44 mmol), followed by addition of 1 droplet of conc. HCl. The mixture was stirred at room temperature for 20 h followed by evaporation ... | CC(=O)N(C(=O)OC(C)(C)C)N1CC(/C=N/N(C)C)=NN(C(=O)OC(C)(C)C)C1=O | null | null | null |
699,589 | ord_dataset-bbd7e53f000345838ad4920a07a169ff | null | 2006-01-01T00:03:00 | true | [CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][C:10]=2[N+:17]([O-])=O)=[O:5])[CH3:2].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25][NH2:26]>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:26][CH2:25][C:24]1[CH:27]=[CH:28][CH:29]=[C:22]([O:21][C... | CCOC(=O)c1cnc2c([N+](=O)[O-])cccc2c1Cl | COc1cccc(CN)c1 | 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 compound prepared in Example 3 was reacted with 3-methoxy-benzylamine according to the method as described in Example 4 and the obtained compound was treated as described in Example 14 to prepare the title compound (yield 85%). | CCOC(=O)c1cnc2c(N)cccc2c1NCc1cccc(OC)c1 | null | 85 | null |
912,736 | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | null | 2009-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:20]([F:23])([F:22])[F:21])=[C:6]([CH:19]=1)[CH2:7][N:8]1[CH2:13][CH2:12][NH:11][C:10]2[N:14]=[CH:15][C:16](I)=[CH:17][C:9]1=2.[C:24]([NH:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)(=[O:26])[CH3:25]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:20]([F:23])([F:22])[F:21])=[C:6]([CH:19]... | FC(F)(F)c1ccc(Cl)cc1CN1CCNc2ncc(I)cc21 | CC(=O)Nc1ccc(B(O)O)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 | 1-[5-Chloro-2-(trifluoromethyl)benzyl]-7-iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (90 mg) was reacted with 4-acetamidophenylboronic acid as in General Procedure 4B to give the title compound as a light gray solid (42% yield). m.p.=244° C., LCMS: m/z=461.24 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 2.13 (3H, s), 3.49 (2H, m... | CC(=O)Nc1ccc(-c2cnc3c(c2)N(Cc2cc(Cl)ccc2C(F)(F)F)CCN3)cc1 | null | 42 | null |
205,742 | ord_dataset-72fffaae67c8473fb9d951cb1b026646 | null | 1990-01-01T00:03:00 | true | [C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[OH-].[NH4+:9]>CN1C(=O)CCC1>[C:1]([O-:6])(=[O:7])[CH2:2][CH2:3][C:4]([NH2:9])=[O:5].[NH4+:9] | O=C1CCC(=O)O1 | null | null | [NH4+] | [OH-] | 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 | null | 3 | To demonstrate that the reactions involved above are, in fact, clean and very nearly quantitative as claimed, the experiments described below were carried out. Succinic anhydride (10 g.; 0.1 mole) was dissolved with magnetic stirring in NMP (100 ml.). Conc. ammonium hydroxide (15 ml; 0.225 mole) was added dropwise with... | NC(=O)CCC(=O)[O-] | null | 99.9 | null |
174,094 | ord_dataset-3844acbccc714c04ab757ec4fca10bd0 | null | 1988-01-01T00:06:00 | true | [Cl:1][C:2]1[C:3](F)=[C:4]([F:19])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([OH:17])=[O:16])[C:7]2=[O:18].[NH2:21][CH2:22][CH:23]1[CH:27]([CH3:28])[CH2:26][NH:25][CH2:24]1.C1CCN2C(=NCCC2)CC1>C(#N)C>[NH2:21][CH2:22][CH:23]1[CH:27]([CH3:28])[CH2:26][N:25]([C:3]2[C:2]([Cl:1])=[C:11]3[C:6]([... | O=C(O)c1cn(C2CC2)c2c(Cl)c(F)c(F)cc2c1=O | CC1CNCC1CN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | C1CCC2=NCCCN2CC1 | null | null | null | null | null | null | null | null | null | 25 | 7 | A mixture of 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.6 g), anhydrous acetonitrile (5 ml), 3-aminomethyl-4-methylpyrrolidine (0.27 g) and 1,8-diazabicyclo[5,4,0]-7-undecene (DBU; 0.3 g) was refluxed for an hour and then stirred at room temperature for 7 hours. The resulting pr... | CC1CN(c2c(F)cc3c(=O)c(C(=O)O)cn(C4CC4)c3c2Cl)CC1CN | null | 33 | null |
1,054,119 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].F[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][C:14]=1[O:21][CH3:22].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][C:14]=2[O:21][CH3:22])=[CH:4][C:3]=1[N+:9... | COc1cc(C=O)ccc1F | Nc1ccc(O)cc1[N+](=O)[O-] | null | O=C([O-])[O-] | [Cs+] | 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 | null | null | 4-Amino-3-nitrophenol (2 g, 13 mmol), 4-fluoro-3-(methyloxy)benzaldehyde (2 g, 13 mmol) and Cs2CO3 (5.1 g, 15.6 mmol) were stirred in dimethylformamide at 100 degrees Centigrade for approximately 18 hours. The reaction was filtered through an Alltech 75 mL Extract-Clean™ filter column packed with glass wool and eluted ... | COc1cc(C=O)ccc1Oc1ccc(N)c([N+](=O)[O-])c1 | null | null | null |
904,909 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5].[N+:12]([O-])([O-:14])=[O:13].[K+]>Cl>[Cl:1][C:2]1[C:3]([C:4]([OH:6])=[O:5])=[C:7]([CH3:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=1 | Cc1cccc(Cl)c1C(=O)O | O=[N+]([O-])[O-] | null | Cl | [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 | null | 0.08 | 2-Chloro-6-methylbenzoic acid (99 mg, 0.58 mmol) was dissolved in conc. hydrochloric acid (1 mL) and cooled in an ice bath. To this solution potassium nitrate in conc. hydrochloric acid (1 mL) was added drop wise. The reaction mixture was stirred for 5 min, then the ice bath was removed and stirring was continued for a... | Cc1c([N+](=O)[O-])ccc(Cl)c1C(=O)O | null | null | null |
377,413 | ord_dataset-846d411edee44814931e062174d7ef12 | null | 1997-01-01T00:09:00 | true | Cl[CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[C:15](=[O:22])[N:14]([CH3:23])[CH2:13][C:12]=23)[N:4]=1.[CH:24]([NH:27][CH:28]([CH3:30])[CH3:29])([CH3:26])[CH3:25]>CN(C)C=O>[CH:24]([N:27]([CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:1... | CN1Cc2c(-c3noc(CCl)n3)ncn2-c2ccccc2C1=O | CC(C)NC(C)C | null | null | null | 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 | null | null | 72 g (212 mmol) of 3-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one were stirred at 80° for 16 hours in 150 ml (1.06 mol) of diisopropylamine and 300 ml of N,N-dimethylformamide. After evaporating the solvent the residue was dissolved in methylene chloride and the s... | CC(C)N(Cc1nc(-c2ncn3c2CN(C)C(=O)c2ccccc2-3)no1)C(C)C | null | 61.7 | null |
1,349,959 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | O=[C:2]([CH2:6][CH3:7])[CH2:3][C:4]#[N:5].[NH2:8][C:9]1[N:13]=[CH:12][NH:11][N:10]=1>C(O)(=O)C>[CH2:6]([C:2]1[CH:3]=[C:4]([NH2:5])[N:10]2[N:11]=[CH:12][N:13]=[C:9]2[N:8]=1)[CH3:7] | CCC(=O)CC#N | Nc1nc[nH]n1 | 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 | 150 | null | A mixture of 3-oxopentanenitrile (1.0 g, 10.3 mmol) and 3-amino-1,2,4-triazole (0.91 g, 10.8 mmol) in 10 mL of acetic acid was heated in a pressure tube at 150° C. for 24 h. The reaction mixture was allowed to cool to room temperature, and solvent was removed in vacuo. The solid was removed via filtration. The filtrate... | CCc1cc(N)n2ncnc2n1 | null | 11.9 | null |
1,596,663 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:13])=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[I:14].[N+:15]([O-])([OH:17])=[O:16]>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:13])=[C:7]([N+:15]([O-:17])=[O:16])[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[I:14] | O=[N+]([O-])O | O=c1cc(O)c2cc(I)c(Cl)cc2[nH]1 | 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 | 25 | 0.25 | 7-Chloro-4-hydroxy-6-iodo-2(1H)-quinolinone (Intermediate 142) (300 mg, 0.933 mmol) was dissolved in nitric acid (1 mL, 22.38 mmol) and the reaction mixture was stirred 15 min at room temperature and heated 30 min at 75° C. After cooling, the reaction mixture was poured into ice water and the precipitate was filtered a... | O=c1[nH]c2cc(Cl)c(I)cc2c(O)c1[N+](=O)[O-] | null | 81.9 | null |
1,180,680 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | Cl[C:2]1[C:7]2[C:8]3[CH2:16][CH2:15][C:14]4[C:10](=[CH:11][N:12]([CH2:17][CH2:18][N:19]5[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]5)[N:13]=4)[C:9]=3[S:26][C:6]=2[N:5]=[CH:4][N:3]=1.[Cl:27][C:28]1[CH:29]=[C:30]([CH:32]=[CH:33][C:34]=1[N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1)[NH2:31].Cl.O1CCOCC1>C(O)(C)C>[Cl:... | CN1CCN(CCn2cc3c(n2)CCc2c-3sc3ncnc(Cl)c23)CC1 | Nc1ccc(N2CCOCC2)c(Cl)c1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CC(C)O | null | null | null | null | null | null | null | null | null | 25 | 0.17 | To a suspension of 6-chloro-2-[2-(4-methylpiperazin-1-yl)ethyl]-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazole (50 mg, 0.13 mmol) and 3-chloro-4-morpholinoaniline (82 mg, 0.39 mmol) in isopropanol (3 mL) was added HCl in dioxane (4M, 0.26 mL, 1.03 mmol). The reaction mixture was sealed in a microwave reaction ... | CN1CCN(CCn2cc3c(n2)CCc2c-3sc3ncnc(Nc4ccc(N5CCOCC5)c(Cl)c4)c23)CC1 | null | null | null |
263,466 | ord_dataset-a7bd0db0684c464bb02ff6a36065fee3 | null | 1993-01-01T00:03:00 | true | [O:1]([CH2:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:29][C:30]1[CH:31]=[C:32]([CH:35]=[C:36](Br)[CH:37]=1)[C:33]#[N:34].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C>[Br... | CC(C)(C)[Si](OCc1ccc(B(O)O)cc1)(c1ccccc1)c1ccccc1 | N#Cc1cc(Br)cc(Br)c1 | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CCO | null | null | null | null | null | null | null | null | null | 80 | 3.5 | A mixture of 1.49 g (3.83 mmoles) of boronic acid derivative from Example 4, 2.0 g (7.67 mmoles) of 3,5-dibromobenzonitrile, and 133 mg (0.1 mmoles) of tetrakistriphenylphosphine in 16 mL toluene and 3.4 mL 95% ethanol with 3.47 mL (6.97 mmoles) of 2 N sodium carbonate was stirred vigorously at 80° C. under nitrogen fo... | CC(C)(C)[Si](OCc1ccc(-c2cc(Br)cc(C#N)c2)cc1)(c1ccccc1)c1ccccc1 | null | null | null |
1,248,558 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | C1(C2[O:12][CH2:11][CH:10]([O:13][CH2:14][CH2:15][O:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[CH2:9][O:8]2)C=CC=CC=1>[Pd].CCOC(C)=O>[O:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]1[O:16][CH2:15][CH2:14][O:13][CH:10]([CH2:11][OH:12])[CH2:9][OH:8] | c1ccc(C2OCC(OCCOC3CCCCO3)CO2)cc1 | null | null | [Pd] | 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 | 25 | 72 | A suspension of 10% palladium on carbon (172 mg, 0.162 mmol) in a solution of 2-phenyl-5[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]-1,3-dioxane (498.9 mg, 1.618 mmol) in EtOAc (32.4 mL) was stirred under H2 at 25° C. for 3 days. The reaction mixture was filtered through a plug of Celite and the filtrate was concentrated in... | OCC(CO)OCCOC1CCCCO1 | null | null | null |
1,025,483 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | [C:1]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:25][C:26]1[N:27]=[C:28]([CH3:31])[S:29][CH:30]=1.O>CN(C)C=O>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH... | COc1ccc(Cl)cc1C(=O)Nc1ncc(C(C)(C)C)s1 | Cc1nc(CCl)cs1 | null | [H-] | [Na+] | 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 | 0.25 | To a solution of Example 74B (0.79 g, 2.43 mmol) in N,N-dimethylformamide (20 mL) was added sodium hydride (Aldrich, 98 mg, 2.43 mmol) and the reaction mixture was stirred for 15 min and 4-(chloromethyl)-2-methylthiazole (0.36 g, 2.43 mmol) was added. The reaction mixture was stirred at room temperature for 18 hr, pour... | COc1ccc(Cl)cc1C(=O)/N=c1\sc(C(C)(C)C)cn1Cc1csc(C)n1 | null | null | null |
1,121,343 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]([OH:19])[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=1.[H-].[Na+].O>CN(C=O)C>[CH:16]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:17]=1[C:8]1[N:7]3[O:19][CH2:2][CH2:3][CH2:4][CH2:5][C:6]3=[N:18][C:9]=1[CH:10]=[N:11]2 | On1c(CCCCCl)nc2cnc3ccccc3c21 | null | null | [H-] | [Na+] | 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 | A stirred solution of 2-(4-chlorobutyl)-1H-imidazo[4,5-c]quinolin-1-ol (0.167 g, 0.606 mmol) in 6 mL of anhydrous DMF was treated with 60% NaH in mineral oil (0.032 g, 0.787 mmol). After 45 minutes the mixture was poured into 20 mL of water and washed with ethyl acetate. The organic portions were combined, washed succe... | c1ccc2c(c1)ncc1nc3n(c12)OCCCC3 | null | 106.2 | null |
433,346 | ord_dataset-386da077ab2340638cada986e2ef0770 | null | 1999-01-01T00:07:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:7]=[CH:6]2 | BrCc1ccccc1 | COc1ccc2[nH]ccc2c1 | null | [H-] | [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 | 5-Methoxy-1H-indole (5.6 g, 21.5 mmol) was reacted with 1.0 g (25 mmol) of 60% sodium hydride and then 3.0 mL (25 mmol) of benzyl bromide by the method described in Example 12, Part D to give crude 5-methoxy-1-(phenylmethyl)-1H-indole. This material was dissolved in 250 mL of methylene chloride, cooled to -5° C., 50 mL... | COc1ccc2c(ccn2Cc2ccccc2)c1 | null | null | null |
45,341 | ord_dataset-becaf7dc22c44672b22e4b94335cbf08 | null | 1978-01-01T00:09:00 | true | Cl[C:2]1[N:3]=[N:4][C:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:6][C:7]=1[CH3:8].[C:16]([NH:19][NH2:20])(=O)[CH3:17]>C(O)CCC>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:5]2[CH:6]=[C:7]([CH3:8])[C:2]3[N:3]([C:16]([CH3:17])=[N:19][N:20]=3)[N:4]=2)=[CH:10][CH:11]=1 | CC(=O)NN | Cc1cc(-c2ccc(Cl)cc2)nnc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 1.0 g. of 3-chloro-6-(p-chlorophenyl)-4-methylpyridazine, 0.62 g. of acetic acid hydrazide and 10 ml. of n-butanol is refluxed for 48 hours. The solvent is removed and the residue dissolved in dichloromethane and filtered through magnesol. The solid from the filtrate is recrystallized from dichloromethane-... | Cc1cc(-c2ccc(Cl)cc2)nn2c(C)nnc12 | null | null | null |
607,466 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [CH2:1]([O:3][C:4](=[O:16])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[C:9]([Cl:15])[CH:8]=1)=[O:6])[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([O:3][C:4](=[O:16])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[C:9]([Cl:15])[CH:8]=1)[OH:6])[CH3:2] | CCOC(=O)C(=O)c1ccc(SC)c(Cl)c1 | null | null | [BH4-] | [Na+] | 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 | 0.25 | A solution of (3-chloro-4-methylsulfanyl-phenyl)-oxo-acetic acid ethyl ester (3.93 g, 15.19 mmol) in methanol (30 mL) was cooled to 0° C. and then treated with sodium borohydride (530.9 mg, 14.03 mmol). The reaction mixture changed from yellow to colorless. The mixture was stirred for 15 min and then quenched with a 1N... | CCOC(=O)C(O)c1ccc(SC)c(Cl)c1 | null | 36.1 | null |
1,681,566 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | C[O:2][C:3](=[O:25])[CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[C:13]([Cl:14])[C:8]=2[O:7][CH:6]=1.CO.[OH-].[Na+]>C1COCC1>[Cl:14][C:13]1[C:8]2[O:7][CH:6]=[C:5]([CH2:4][C:3]([OH:25])=[O:2])[C:9]=2[CH:10]=[CH:11][C:12]=1[O:15][CH2:16][C:17]1[CH:22]... | COC(=O)Cc1coc2c(Cl)c(OCc3ccc(Cl)cc3Cl)ccc12 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | 25 | 2 | To a mixture of methyl(7-chloro-6-((2,4-dichlorobenzyl)oxy)-1-benzofuran-3-yl)acetate (218.9 mg), MeOH (2.0 mL) and THF (dry) (2.0 mL) was added 1N NaOH (1.643 mL) at room temperature. The mixture was stirred at room temperature for 2 h. The residue was concentrated. The residue was neutralized with 1N HCl, and the mix... | O=C(O)Cc1coc2c(Cl)c(OCc3ccc(Cl)cc3Cl)ccc12 | null | 87.1 | null |
725,349 | ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | null | 2006-01-01T00:08:00 | true | [F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]2[C:3]=1[C:4](=[O:26])[N:5]([CH2:13][CH:14]([C:20]1([CH3:25])OCC[O:21]1)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:6]2=[O:12].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[F:11][C:8]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]2[C:7]=1[C:6](=[O:12])[N:5]([CH2:13][CH:14]([C:20](=[O:21])[CH3:25])[C:15]([O:... | CCOC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C1(C)OCCO1 | null | null | Cc1ccc(S(=O)(=O)O)cc1 | null | 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 | null | Ethyl 2-(4,7-difluoro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (95 mg, 19%) in the same manner as described in the above example 6 (20) from ethyl 3-(4,7-difluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.58 g, 1.57 mmol) and p-toluenesulfonic acid m... | CCOC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C(C)=O | null | null | null |
483,379 | ord_dataset-cb5c1a9eddff4790b1bd650617c32d34 | null | 2000-01-01T00:11:00 | true | [C:1]1([C:7]2[CH:12]=[CH:11][C:10]([Mg]Br)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:15]1[C:22]([Cl:23])=[N:21][C:19](Cl)=[N:18][C:16]=1[Cl:17]>C1C=CC=CC=1>[C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:12]=[CH:11][C:10]([C:19]2[N:21]=[C:22]([Cl:23])[N:15]=[C:16]([Cl:17])[N:18]=2)=[CH:9][CH:8]=1 | Br[Mg]c1ccc(-c2ccccc2)cc1 | Clc1nc(Cl)nc(Cl)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | 0 | 1.5 | A mixture of 4-phenyl-phenyl magnesium bromide (prepared from 4-bromobiphenyl (7.75 g, 33 mmol) and magnesium turnings (0.83 g, 35 mmol) in 40 mL ether) and cyanuric chloride (4.00 g, 21.7 mmol) in benzene (90 mL) was stirred at 0° C. for 90 minutes. The reaction was evaporated to dryness, and the residue was flash chr... | Clc1nc(Cl)nc(-c2ccc(-c3ccccc3)cc2)n1 | null | 42.7 | null |
944,058 | ord_dataset-ed680843f6d14f5c9901869b2a06b4a4 | null | 2010-01-01T00:03:00 | true | [CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([NH:10]C(OC(C)(C)C)=O)[C@@H:7]([OH:18])[CH2:6]1)=[O:4].[ClH:19]>O1CCOCC1>[ClH:19].[CH3:1][O:2][C:3]([C@H:5]1[CH2:6][C@H:7]([OH:18])[C@@H:8]([NH2:10])[CH2:9]1)=[O:4] | COC(=O)[C@@H]1C[C@H](NC(=O)OC(C)(C)C)[C@@H](O)C1 | null | null | Cl | 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 | null | null | A solution of (1S,2S,4R)—N—Boc-1-amino-2-hydroxycyclopentane-4-carboxylic acid methyl ester (0.2 g) in 4M HCl in dioxane (4 ml) was stirred under an argon atmosphere at r.t. for 2 hrs. The reaction mixture was concentrated to give (1R,3S,4S)-3-amino-4-hydroxy-cyclopentanecarboxylic acid methyl ester hydrochloride (165 ... | COC(=O)[C@@H]1C[C@H](N)[C@@H](O)C1 | null | null | null |
1,236,526 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[C:12]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])O.[Na+]>C(OC(=O)C)(=O)C>[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:12]([O:20][CH2:21][CH3:22... | CCOC(=O)CC(=O)OCC | O=Cc1ccccc1[N+](=O)[O-] | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | 32.3 g (0.21 mol) of 2-nitrobenzaldehyde and 35.0 g (0.21 mol) of diethyl malonate were added to 100 mL of acetic anhydride at room temperature. 27.0 g (0.32 mol) of sodium hydrogen carbonate was added to this mixture, and the resulting mixture was allowed to react overnight at 100° C. The reaction mixture was concentr... | CCOC(=O)C(=Cc1ccccc1[N+](=O)[O-])C(=O)OCC | null | 60.1 | null |
1,753,948 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | Br[CH2:2][C:3]1[C:8]([Cl:9])=[CH:7][N:6]=[C:5]([Cl:10])[CH:4]=1.[F:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O>[Cl:10][C:5]1[CH:4]=[C:3]([CH2:2][C:15]2[CH:14]=[CH:13][C:12]([F:11])=[CH:17][CH:16]=2)[C:8]([Cl:9])=[CH:7][N:6]=1 | OB(O)c1cccc(F)c1 | Clc1cc(CBr)c(Cl)cn1 | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | O | null | null | null | null | null | null | null | null | null | 80 | 3 | To a solution of 4-bromomethyl-2,5-dichloro-pyridine (500 mg, 2.08 mmol) in toluene (10 mL) was added with stirring the [1,1-bis(diphenylphos-phino)ferrocene]dichloropalladium DCM complex (74 mg, 0.101 mmol), B-(3-fluorophenyl)-boronic acid (290 mg, 2.08 mmol) and sodium carbonate (440 mg, 4.15 mmol) in water (2 mL). T... | Fc1ccc(Cc2cc(Cl)ncc2Cl)cc1 | null | 45.2 | null |
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