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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
721,182 | ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | null | 2006-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[CH2:10][CH2:11][N:12]2C(=O)C3=CC=CC=C3C2=O)[CH:5]=[CH:6][CH:7]=1.CN>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[CH2:10][CH2:11][NH2:12])[CH:5]=[CH:6][CH:7]=1 | O=C1c2ccccc2C(=O)N1CC/C=C/c1cccc(Cl)c1 | null | null | CN | 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 | null | A solution of trans-N-[4-(3-chlorophenyl)-but-3-enyl]-phthalimide (0.50 g) and methylamine (2 M in tetrahydrofuran, 8 mL) in 20 mL ethanol was heated to reflux for 4 h. The solution was cooled to rt and the solvent was removed in vacuo. The resulting residue was dissolved in ethyl acetate and extracted 3 times with 1 M... | NCC/C=C/c1cccc(Cl)c1 | null | 68.6 | null |
391,050 | ord_dataset-4bc8addcf9cf4845817557760d62d5b5 | null | 1998-01-01T00:02:00 | true | P(Cl)(Cl)(Cl)(Cl)Cl.[C:7]([CH2:9][C:10]([OH:12])=O)#[N:8].[F:13][C:14]([F:23])([F:22])[C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[F:13][C:14]([F:22])([F:23])[C:15]1[CH:16]=[CH:17][C:18]([NH:19][C:10](=[O:12])[CH2:9][C:7]#[N:8])=[CH:20][CH:21]=1 | N#CCC(=O)O | Nc1ccc(C(F)(F)F)cc1 | null | ClP(Cl)(Cl)(Cl)Cl | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O | null | null | null | null | null | null | null | null | null | 20 | 0.5 | Phosphorus pentachloride (83.3 g; 0.40 mol) is introduced into a solution of cyanoacetic acid (34.0 g; 0.40 mol) in 1,2 l of dichloromethane and the mixture is heated under reflux for 30 minutes. 4-Trifluoromethylaniline (41.0 g, 0.26 mol) is then introduced into said mixture within about 10 minutes and the reaction mi... | N#CCC(=O)Nc1ccc(C(F)(F)F)cc1 | null | 93 | null |
499,945 | ord_dataset-18e9ed24dbd44e98b33bdc22aa7580a8 | null | 2001-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH2:5][NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=2)[C:10](=[O:19])[NH:9][N:8]=1.Br[CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].C(=O)([O-])[O-].[K+].[K+].O>CN1CCCC1=O>[C:30]([O:29][C:27]([CH2:26][N:9]1[N:8]=[C:... | CC(C)(C)OC(=O)CBr | COc1ccc(CNc2n[nH]c(=O)c3ccc(C#N)cc23)cc1Cl | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | O | null | null | null | null | null | null | null | null | null | 80 | 4 | 4-(3-Chloro-4-methoxybenzyl)amino-6-cyanol-1(2H)-phthalazinone (0.20 g) prepared in Example 21 was dissolved in 5 ml of N-methyl-2-pyrrolidinone, followed by the addition of 0.14 g of t-butyl bromoacetate and 0.24 g of potassium carbonate. The obtained mixture was stirred at 80° C. for 4 hours and poured into water, fo... | COc1ccc(CNc2nn(CC(=O)OC(C)(C)C)c(=O)c3ccc(C#N)cc23)cc1Cl | null | 153.6 | null |
649,874 | ord_dataset-271c0b74f4794a06992957029b3151ba | null | 2004-01-01T00:10:00 | true | CC1C=CC(S(O[CH2:12][C@@H:13]2[O:25][C:24]3[C:20]4=[CH:21][O:22][N:23]=[C:19]4[CH:18]=[CH:17][C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[NH:26]1[CH2:31][CH:30]=[C:29]([C:32]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[NH:34][CH:33]=2)[CH2:28][CH2:27]1>CS(C)=O>[NH:34]1[C:35]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:32]([... | C1=C(c2c[nH]c3ccccc23)CCNC1 | Cc1ccc(S(=O)(=O)OC[C@H]2COc3ccc4nocc4c3O2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 77.5 | null | (2R)-2,3-Dihydro[1,4]dioxino[2,3-e][2,1]benzisoxazol-2-ylmethyl 4-methyl-benzenesulfonate (0.60 g, 1.66 mmole) and 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (0.98 g, 4.90 mmole) were combined in 30 mL of DMSO under nitrogen. This solution was heated to 75-80° C. under nitrogen for 6 hours. After completion, the reac... | C1=C(c2c[nH]c3ccccc23)CCN(CC2COc3ccc4nocc4c3O2)C1 | null | null | null |
142,246 | ord_dataset-84dc0c9e5fb4424687194ef8d14d1c22 | null | 1986-01-01T00:04:00 | true | Cl[SiH:2](Cl)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[S:10]([C:26]1[CH:31]=[C:30]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:29]=[C:28]([C:36]([CH3:39])([CH3:38])[CH3:37])[C:27]=1[OH:40])[C:11]1[CH:16]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:14]=[C:13]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:12]=1[OH:25].C(N(CC)CC)C>>... | CC(C)(C)c1cc(Sc2cc(C(C)(C)C)cc(C(C)(C)C)c2O)c(O)c(C(C)(C)C)c1 | Cl[SiH](Cl)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | Utilizing the procedure of Example 1, this compound is prepared from 5.3 grams (0.03 mole) dichlorophenylsilane, 13.3 grams (0.03 mole) 2,2'-thio-bis(4,6-di-t-butylphenol), and 6.1 grams (0.06 mole) triethylamine. Recrystallization from acetone gives 6.7 grams (41% yield) of white solid, mp 175°-177° C. | CC(C)(C)c1cc2c(c(C(C)(C)C)c1)O[SiH](c1ccccc1)Oc1c(cc(C(C)(C)C)cc1C(C)(C)C)S2 | null | 40.8 | null |
746,175 | ord_dataset-4b705442211b4a3988e26d5f65098160 | null | 2006-01-01T00:12:00 | true | [C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]3[CH:18]=[C:19]([Cl:26])[C:20]([C:22]([F:25])([F:24])[F:23])=[CH:21][C:16]=3[N:15]=[C:14]2[C:27](Cl)([CH3:29])[CH3:28])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[N-:31]=[N+:32]=[N-:33].[Na+].O>CN(C=O)C>[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C... | CC(=O)OCCc1ccc(-n2c(C(C)(C)Cl)nc3cc(C(F)(F)F)c(Cl)cc32)cc1 | [N-]=[N+]=[N-] | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 25 | 5.5 | A mixture of 2-{4-[6-chloro-2-(1-chloro-1-methylethyl)-5-(trifluoromethyl)-1H-benzimidazol-1-yl]phenyl}ethyl acetate (step 1, 273 mg, 0.68 mmol), sodium azide (88 mg, 1.36 mmol), KI (112 mg, 0.68 mmol) in DMF (8 ml) was stirred under nitrogen at room temperature for 5.5 h. The reaction mixture was poured into water (5 ... | CC(=O)OCCc1ccc(-n2c(C(C)(C)N=[N+]=[N-])nc3cc(C(F)(F)F)c(Cl)cc32)cc1 | null | 42 | null |
533,007 | ord_dataset-b1a34bc8c1204d51a772ed27396c794e | null | 2002-01-01T00:02:00 | true | [C:1]([C:11]1[S:12][C:13]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:14][C:15]=1[NH:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=[O:18])([O:3]CC1C=CC=CC=1)=[O:2]>CCO.[Pd]>[C:1]([C:11]1[S:12][C:13]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:14][C:15]=1[NH:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:... | Cc1ccc(NC(=O)Nc2cc(C(C)(C)C)sc2C(=O)OCc2ccccc2)cc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of N-(2-carbobenzyloxy-5-tert-butyl-3-thienyl)-N′-(4-methylphenyl)urea (0.19 g, 0.40 mmol) in EtOH (19 mL) was added 10% Pd/C (0.010 g). The resulting suspension was treated with H2 (52 psi) in a Parr® shaker for 18 h. The slurry was filtered through a pad of Celite® and concentrated under reduced pressur... | Cc1ccc(NC(=O)Nc2cc(C(C)(C)C)sc2C(=O)O)cc1 | null | 90.2 | null |
914,486 | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | null | 2009-01-01T00:10:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].[N:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[C:23]=[S:24]>CN(C)C=O>[C:25]1([NH:22][C:23]([N:13]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:19]3[C:11]([C:5]3[CH:6]=[CH... | S=C=Nc1ccccc1 | COc1ccc(-c2c[nH]c3ncccc23)cc1OC | 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 | 0.25 | 3-(3,4-Dimethoxy-phenyl)-1H-pyrrolo-[2,3-b]pyridine 1 (50 mg, 0.20 mmol) was dissolved in N,N-dimethylformamide (4 mL). Sodium hydride (10 mg, 0.24 mmol, 60% dispersion in mineral oil) was added. The reaction mixture was stirred for 15 minutes at room temperature. 1-Isothiocyanatobenzene (35 μL, 0.29 mmol) was added an... | COc1ccc(-c2cn(C(=S)Nc3ccccc3)c3ncccc23)cc1OC | null | 48.8 | null |
890,315 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [ClH:1].CO.[CH2:4]([N:11]1[CH2:15][CH2:14][CH:13]([NH:16][C:17]2[N:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[C:25]([NH:27][O:28]C3CCCCO3)=[O:26])=[CH:19][CH:18]=2)[CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CO>[ClH:1].[ClH:1].[CH2:4]([N:11]1[CH2:15][CH2:14][CH:13]([NH:16][C:17]2[N:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[... | O=C(/C=C/c1ccc(NC2CCN(Cc3ccccc3)C2)nc1)NOC1CCCCO1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 20 | 2 | A solution of 10% HCl-MeOH solution (0.75 ml) was added to a mixture of (2E)-3-{6-[(1-benzyl-3-pyrrolidinyl)amino]-3-pyridyl}-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide (170 mg) in MeOH 3 ml) and stirred at 15-25° C. for 2 hours. The reaction mixture was evaporated in vacuo and the residue was triturated with small amou... | O=C(/C=C/c1ccc(NC2CCN(Cc3ccccc3)C2)nc1)NO | null | null | null |
839,762 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:12])[CH:8]=2)[CH:3]=1.[CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O)=[O:14].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC>[CH3:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH:13]=[O:14])[CH:11]=[CH:... | Cc1ccc2cc(Br)ccc2c1 | O=Cc1ccccc1B(O)O | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | null | null | null | null | null | null | null | null | null | null | null | null | Under an atmospheric argon gas flow, 2-bromo-6-methylnaphthalene in an amount of 6.6 g (30 mmol), 2-formylphenylboronic acid in an amount of 5.4 g (36 mmol), (tetrakistriphenylphosphine)palladium in an amount of 0.7 g (0.6 mmol), 2N sodium carbonate aqueous solution in an amount of 45 milliliter and dimethoxyethane in ... | Cc1ccc2cc(-c3ccccc3C=O)ccc2c1 | null | 91 | null |
606,889 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [F:1][C:2]1[C:3]([F:41])=[CH:4][C:5]2[C:10]3[C:11]4[C:38](=[O:39])[NH:37][C:36](=[O:40])[C:12]=4[C:13]4[C:14]5[C:19]([N:20]([C@@H:22]6[O:29][C@H:28]([CH2:30][OH:31])[C:27]([F:33])([F:32])[C@H:25](O)[C@H:23]6[OH:24])[C:21]=4[C:9]=3[NH:8][C:6]=2[CH:7]=1)=[CH:18][C:17]([F:34])=[C:16]([F:35])[CH:15]=5.C1(P(C2C=CC=CC=2)C2C=... | O=C1NC(=O)c2c1c1c3cc(F)c(F)cc3[nH]c1c1c2c2cc(F)c(F)cc2n1[C@@H]1O[C@H](CO)C(F)(F)[C@H](O)[C@H]1O | null | null | CC(C)OC(=O)/N=N/C(=O)OC(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 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 | 18 | To a solution of 2,3,9,10-tetrafluoro-12-(4-deoxy-4, 4-difluoro-β-D-glucopyranosyl)-6, 7, 12, 13-tetrahydro(5H)indolo[2, 3-a]pyrrolo[3, 4-c]carbazole-5, 7-dione (0.035 g, 0.060 mmol) in 4 mL of dry THF was added triphenylphosphine (0.048 g, 0.18 mmol) and DIAD (0.035 mL, 0.18 mmol), at room temperature under Ar. The re... | O=C1NC(=O)c2c1c1c3cc(F)c(F)cc3[nH]c1c1c2c2cc(F)c(F)cc2n1[C@@H]1O[C@@H]2CO[C@H]([C@H]1O)C2(F)F | null | 26.7 | null |
1,372,939 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([CH:14]=[O:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[OH:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1 | COc1ccc(-c2ccc(C=O)s2)cc1 | BrCc1ccccc1 | null | null | null | null | null | null | null | 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 the product of step 1 (0.56 g, 2.55 mmol) and benzyl bromide (0.5 g, 3.2 mmol) using the procedure of Example 159, step 2 with 64% yield (0.6 g). | COc1ccc(-c2ccc(C(O)c3ccccc3)s2)cc1 | null | 64 | null |
1,121,073 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[C:14](=[C:16]([C:20]([O:22]C)=O)[CH:17]=[CH:18][CH:19]=3)[N:15]=2)=[CH:7][CH:6]=1)[CH3:3].O.[NH3:25]>>[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[C:14](=[C:16]([C:20]([NH2:25])=[O:22])[CH:17]=[CH:18][CH:19]=3)[N:15]=2)=[CH:7][CH:6... | COC(=O)c1cccc2oc(-c3ccc(CN(C)C)cc3)nc12 | N | null | null | 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 | 30 | 1 | Methyl 2-(4-((dimethylamino)methyl)phenyl)benzo[d]oxazole-4-carboxylate (40 mg, 0.13 mmol) and ammonia water (17.2 mg, 0.52 mmol) were added and the mixture was stirred at 30° C. for 1 h. The resulting mixture was evaporated under reduced pressure and purified by pre-HPLC. 2-(4-((dimethylamino)methyl)phenyl)benzo[d]oxa... | CN(C)Cc1ccc(-c2nc3c(C(N)=O)cccc3o2)cc1 | null | 41.7 | null |
1,465,580 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:8]1[N:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:9]=1[C:10]#[N:11].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:16][C:14]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[C:8]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[N:15]=1 | Cc1ccc(C#N)c(Cl)n1 | C1CNCCN1 | null | O=C([O-])[O-] | [K+] | 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 | 60 | 8 | Piperazine (1.13 g) and 2-chloro-6-methylnicotinonitrile (500 mg) were dissolved in DMF (15 ml), and K2CO3 (1.36 g) was added thereto, followed by stirring at 60° C. overnight. The reaction mixture was concentrated under reduced pressure, and then a saturated aqueous sodium hydrogen carbonate solution was added thereto... | Cc1ccc(C#N)c(N2CCNCC2)n1 | null | 94.8 | null |
467,843 | ord_dataset-8cd3720738054d76b936f66e14d8cba6 | null | 2000-01-01T00:06:00 | true | [Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([O:14][CH3:15])[C:8]([O:12][CH3:13])=[N:9]2)=[C:4]([CH2:16]Br)[CH:3]=1.C(N(CC)CC)C.Cl.[C:26]([O:30][C:31](=[O:34])[CH2:32][NH2:33])([CH3:29])([CH3:28])[CH3:27]>C(#N)C>[C:26]([O:30][C:31](=[O:34])[CH2:32][NH:33][CH2:16][C:4]1[CH:3]=[C:2]([Br:1])[CH:11]=[C:10]2[C:5]=1[N:6]=[C:... | CC(C)(C)OC(=O)CN | COc1nc2cc(Br)cc(CBr)c2nc1OC | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CC#N | null | null | null | null | null | null | null | null | null | null | null | 850 mg (2.35 mmol) of 7-bromo-5-bromomethyl-2,3-dimethoxy-quinoxaline, 0.982 ml of triethylamine and 719 mg of glycine tert-butyl ester hydrochloride are dissolved in 15 ml of acetonitrile and the solution is stirred at reflux for 18 hours. The mixture is concentrated by evaporation and the residue is dissolved in diet... | COc1nc2cc(Br)cc(CNCC(=O)OC(C)(C)C)c2nc1OC | null | null | null |
487,100 | ord_dataset-7b02d32cc502407f94aea8e5caf405a2 | null | 2000-01-01T00:12:00 | true | [N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:7]=[C:8]([CH2:13][C:14]#[N:15])[CH:9]=[CH:10][C:11]=1[F:12].C(=O)([O-])O.[Na+]>>[N+:1]([C:9]1[CH:10]=[C:11]([F:12])[C:6]([F:5])=[CH:7][C:8]=1[CH2:13][C:14]#[N:15])([O-:4])=[O:2] | O=[N+]([O-])O | N#CCc1ccc(F)c(F)c1 | null | O=C([O-])O | [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 | 0 | 15 | Fuming nitric acid (25 ml) was stirred with cooling (ice/water bath) and 3,4-difluorophenylacetonitrile (5 g, 32.7 mmol) was added dropwise. The mixture was left to stir for 15 h and was then poured onto ice. The mixture was neutralised with sodium hydrogen carbonate and extracted with dichloromethane. The combined org... | N#CCc1cc(F)c(F)cc1[N+](=O)[O-] | null | null | null |
294,027 | ord_dataset-bb4579c57ddc48c6a01fad97dacb6293 | null | 1994-01-01T00:08:00 | true | [C:1]([C:4]1[CH:5]=[C:6]2[C:13](=[O:14])[N:12]3[C:15](=[O:22])[C:16]([CH3:21])([CH:18]([CH3:20])[CH3:19])[N:17]=[C:11]3[C:7]2=[N:8][C:9]=1[CH3:10])(=[O:3])[CH3:2].[H-].[Na+].[CH2:25]([OH:31])[C:26]1[O:30][CH:29]=[CH:28][CH:27]=1.C(O)(=O)C>O1CCCC1>[C:1]([C:4]1[C:9]([CH3:10])=[N:8][C:7]([C:11]2[NH:12][C:15](=[O:22])[C:16... | OCc1ccco1 | CC(=O)c1cc2c(nc1C)C1=NC(C)(C(C)C)C(=O)N1C2=O | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CC(=O)O | null | null | null | null | null | null | null | null | null | 25 | 8 | A solution of 1.0 g of 7-acetyl-2,8-dimethyl-2-isopropyl-5H-imidazo[1',2':1,2]pyrrolo[3,4-b]-pyridine-3(2H),5-dione in 50 mL tetrahydrofuran is added dropwise to a preformed mixture of 0.03 g sodium hydride and 0.35 mL furfuryl alcohol in 50 mL tetrahydrofuran. The reaction mixture is stirred at room temperature overni... | CC(=O)c1cc(C(=O)OCc2ccco2)c(C2=NC(C)(C(C)C)C(=O)N2)nc1C | null | null | null |
180,015 | ord_dataset-ed5a3d1f8dc744759e7fa1c320a44e59 | null | 1988-01-01T00:11:00 | true | [I:1]Cl.[NH2:3][C:4]1[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7].CCOCC>C(O)(=O)C>[NH2:3][C:4]1[C:12]([CH3:13])=[CH:11][C:10]([I:1])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7] | ClI | Cc1cccc(C(=O)O)c1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | CCOCC | null | null | null | null | null | null | null | null | null | null | null | Iodine monochloride (28.9 g) was added over 0.5 hours to a stirred solution of 2-amino-3-methylbenzoic acid (24.5 g) (Aldrich Chemical Co. Ltd.) in acetic acid (250 cm3). After 24 hours ether (250 cm3) was added and the mixture was filtered. The solid material was dried in vacuo to afford the title compound, m.p. 214° ... | Cc1cc(I)cc(C(=O)O)c1N | null | null | null |
812,551 | ord_dataset-892acf7477db4d3a8a8559f004a7c0a2 | null | 2008-01-01T00:03:00 | true | [CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]=[CH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[N:6]=1)=[O:4]>C(O)(=O)C.O=[Pt]=O>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[NH:6]1)=[O:4] | COC(=O)c1cccc(C=CC(=O)OC(C)(C)C)n1 | null | null | O=[Pt]=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | 72 | Compound 2 (1.0 g) is dissolved in glacial acetic acid (10 ml) and PtO2 (100 mg) is added. Hydrogenation is carried out in Parr shaker at 55 psi for 3 days. The catalyst is removed by filtration through Celite, and the solvent is evaporated to give the desired product as a yellow oil. 1H NMR (CD3OD) δ 3.73 (s, 3H), 3.4... | COC(=O)C1CCCC(CCC(=O)OC(C)(C)C)N1 | null | null | null |
447,370 | ord_dataset-a4f0b79f6b9847168861270b79f84afa | null | 1999-01-01T00:11:00 | true | [C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH:12]=[CH:13][O:14]C)[CH2:8][CH2:9][C:10]#[N:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>C(OCC)C>[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:12][CH:13]=[O:14])[CH2:8][CH2:9][C:10]#[N:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1 | COC=CC(CCC#N)(c1ccccc1)c1ccccc1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | 25 | 16 | To a solution of 4,4-diphenyl-6-methoxyhex-5-enenitrile (4.0 g, 14.4 mmol) in diethylether (60 mL) was added HCl (2 mL, 37 %). The reaction mixture was stirred at room temperature for 16 hr and then the solvent was evaporated in vacuo . The residue was dissolved in dichloro- methane and filtered through a plug of silic... | N#CCCC(CC=O)(c1ccccc1)c1ccccc1 | null | 99.7 | null |
758,754 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | Br[C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[CH3:10][O:11][C:12]([C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)=[O:13].C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.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=C... | Cc1ccc(N)cc1Br | COC(=O)c1ccc(B(O)O)cc1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | null | null | null | null | null | null | null | null | null | null | 90 | null | 3-Bromo-4-methylaniline (744 mg, 4.0 mmol), (4-methoxycarbonylphenyl)boronic acid (864 mg, 4.8 mmol), tetrakis(triphenylphosphine)palladium (100 mg, 0.087 mmol) and caesium carbonate (2.4 g, 7.37 mmol) were mixed in DME (30 ml) and heated at 90° C. for 20 h. The reaction was absorbed onto silica applied to a silica SPE... | COC(=O)c1ccc(-c2cc(N)ccc2C)cc1 | null | 51.8 | null |
975,625 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | [OH-:1].[Na+:2].[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[C:13]4[CH2:27][O:26][C:25](=[O:28])[C:14]=4[CH:15]=[C:16]4[C:24]=3[C:20]3[O:21][CH2:22][O:23][C:19]=3[CH:18]=[CH:17]4)=[CH:11][C:6]=2[O:5][CH2:4]1>CO>[Na+:2].[O:23]1[C:19]2[CH:18]=[CH:17][C:16]([C:15]3[C:14]([CH2:25][OH:28])=[C:13]([C:27]([O-:1])=[O:26])[CH:12]=[C... | [OH-] | O=C1OCc2c1cc1ccc3c(c1c2-c1ccc2c(c1)OCO2)OCO3 | null | [Na+] | 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 | 70 | 1 | 1 N aqueous NaOH solution (2.9 mL) was added to the solution of 2 (100 mg, 0.29 mmol) in MeOH (10 mL). The mixture was stirred at 70° C. for 1 h. The solvent was evaporated to give a crude product, which was purified by silica gel column chromatography using CH2Cl2/MeOH (3:1, v/v) to afford 3 (110 mg, 98%) as a white p... | O=C([O-])c1cc2ccc3c(c2c(-c2ccc4c(c2)OCO4)c1CO)OCO3 | null | 98 | null |
1,582,048 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | C([O:4][C@@H:5]([CH3:41])[C:6]([NH:8][CH2:9][C@@H:10]1[CH2:15][O:14][C@@H:13]([C@H:16]2[O:20][N:19]=[C:18]([C:21]3[CH:26]=[C:25]([C:27](=[O:39])[NH:28][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([F:36])=[C:32]([O:37][CH3:38])[CH:31]=4)[N:24]=[C:23]([CH3:40])[N:22]=3)[CH2:17]2)[CH2:12][O:11]1)=[O:7])(=O)C.[OH-].[Li+]>C(#N)C.CC... | COc1cc(CNC(=O)c2cc(C3=NO[C@H]([C@H]4CO[C@H](CNC(=O)[C@H](C)OC(C)=O)CO4)C3)nc(C)n2)ccc1F | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CC#N | null | null | null | null | null | null | null | null | null | null | 3 | To a stirred solution of (S)-1-(((2R,5R)-5-((S)-3-(6-(4-fluoro-3-methoxybenzylcarbamoyl)-2-methylpyrimidin-4-yl)-4,5-dihydroisoxazol-5-yl)-1,4-dioxan-2-yl)methylamino)-1-oxopropan-2-yl acetate (0.11 g, 0.192 mmol) in ACN (3 mL) was added 2.5M lithium hydroxide (1.151 mL, 2.88 mmol) at RT. The reaction mixture was stirr... | COc1cc(CNC(=O)c2cc(C3=NO[C@H]([C@H]4CO[C@H](CNC(=O)[C@H](C)O)CO4)C3)nc(C)n2)ccc1F | null | 53.9 | null |
797,879 | ord_dataset-a2d74266062e4398bc26c4f876903ab8 | null | 2007-01-01T00:11:00 | true | CS([C:5]1[N:10]=[CH:9][C:8]([C:11]2[O:15][C:14]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:13]([C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[C:27](=[O:31])[CH2:26][CH2:25]4)[CH:12]=2)=[CH:7][N:6]=1)(=O)=O.[NH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>>[N:32]1([C:5]2[N:10]=[CH:9][C:8]([C:11]3[O:15][C:14]([C:... | C1CNCCN1 | CS(=O)(=O)c1ncc(-c2cc(-c3ccc4c(c3)CCC4=O)c(-c3ccncc3)o2)cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound (0.10 g, 65%) was prepared from the product of Example 7 Step 6 and piperazine using the method of Example 7 Step 7; MS(ES+) m/e 438 [M+H]+. | O=C1CCc2cc(-c3cc(-c4cnc(N5CCNCC5)nc4)oc3-c3ccncc3)ccc21 | null | 65 | null |
134,400 | ord_dataset-b76b52f4448a4eedb28ffcd8f902046a | null | 1985-01-01T00:09:00 | true | [CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[CH3:13][S:14]([O:17][C@@H:18]([CH3:22])[C:19](Cl)=[O:20])(=[O:16])=[O:15]>ClC1C=CC=CC=1Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:19](=[O:20])[CH:18]([O:17][S:14]([CH3:13])(=[O:16])=[O:15])[CH3:22])[CH:7... | COc1ccc2ccccc2c1 | C[C@H](OS(C)(=O)=O)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Clc1ccccc1Cl | null | null | null | null | null | null | null | null | null | null | 25 | null | 791 Mg (5.00 mmols) of β-methoxynaphthalene and 933 mg (5.00 mmols) of (S)-2-(methylsulfonyloxy)propionyl chloride were dissolved in 5 ml of anhydrous o-dichlorobenzene, followed by stirring at room temperature. To the solution was added 296 mg of dry ferric sulfate obtained by drying ferric sulfate heptahydrate at 150... | COc1ccc2cc(C(=O)C(C)OS(C)(=O)=O)ccc2c1 | null | null | null |
366,819 | ord_dataset-b18df02d6e9345faa0f2dae281a0870a | null | 1997-01-01T00:06:00 | true | [CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:17])([C:7]3[CH:15]=[CH:14][C:13]([SH:16])=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:18].C(=O)([O-])[O-].[K+].[K+].Cl[C:26]1[S:27][C:28]2[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][C:29]=2[N:30]=1.CN(C)C=O>C(OCC)(=O)C>[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:17])([C:7... | CN1C(=O)CC[C@]2(C)c3ccc(S)cc3CC[C@@H]12 | O=[N+]([O-])c1ccc2sc(Cl)nc2c1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-8-mercapto-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (100 mg, 0.38 mmol), potassium carbonate (158 mg, 1.14 mmol), 2-chloro-5-nitrobenzothiazole (99 mg, 0.46 mmol) and 1 mL of anhydrous dimethylformamide, fitted with a reflux cond... | CN1C(=O)CC[C@]2(C)c3ccc(Sc4nc5cc([N+](=O)[O-])ccc5s4)cc3CC[C@@H]12 | null | 58.1 | null |
1,605,801 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | Cl[C:2]1[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]2[C:19](=[O:26])[NH:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])=[O:15])[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:35]2[CH:36]=[N:37][C:38]([NH2:41])=[N:39][CH:40]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=... | CC1(C)OB(c2cnc(N)nc2)OC1(C)C | Cc1cc(C)c(CNC(=O)c2cc(Cl)nc3c2cnn3C(C)C)c(=O)[nH]1 | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | To a 5-mL microwave vial was added DMSO (2 mL) and it was degassed with nitrogen for 5 min. Next added 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (70 mg, 0.187 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyrimidinamine (49.7 mg... | Cc1cc(C)c(CNC(=O)c2cc(-c3cnc(N)nc3)nc3c2cnn3C(C)C)c(=O)[nH]1 | null | 17.3 | null |
1,119,240 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | [NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[S:19](=[O:21])(=[O:20])[N:18]([CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:17](=[O:28])[CH2:16]2)=[C:11]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:10]=1.C(N(C(C)C)CC)(C)C.[CH3:46][S:47](Cl)(=[... | C[Si](C)(C)CCN1C(=O)CN(c2ccc(C[C@@H]3CCCC[C@H]3N)cc2OCc2ccccc2)S1(=O)=O | CS(=O)(=O)Cl | null | Cl | 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 | 25 | 14 | To a solution of 5-[4-((1S*,2R*)-2-aminocyclohexylmethyl)-2-benzyloxy-phenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (153 mg, 0.238 mmol) and diisopropylethylamine (92 mg, 0.712 mmol) in methylene chloride (5 mL) is added methanesulfonyl chloride (30 mg, 0.258 mmol) and the mixture is stirred ... | C[Si](C)(C)CCN1C(=O)CN(c2ccc(C[C@@H]3CCCC[C@H]3NS(C)(=O)=O)cc2OCc2ccccc2)S1(=O)=O | null | null | null |
1,133,995 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:29]=[C:30]([N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[CH:31]=1)[C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21](S(C)(=O)=O)[N:20]=2)=[CH:10][CH:9]=1)=[O:6].[CH:38]([NH:41][CH3:42])([CH3:40])[CH3:39]>>[F:1][C:2]1[CH:3]=[C... | CNC(C)C | CS(=O)(=O)c1nccc(Oc2ccc(NC(=O)c3cc(F)cc(N4CCCCC4)c3)c3ccccc23)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 | null | null | Compound is prepared from 3-fluoro-N-[4-(2-methanesulfonyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-5-piperidin-1-yl-benzamide and N-isopropylmethylamine according to conditions described in general procedure C. Mp: 102-104° C.; 1H NMR (400 MHz, DMSO-d6) δ 0.94 (bs, 6 H), 1.58 (s, 6 H), 2.70 (bs, 1 H), 3.26-3.31 (m, 7 H), 6... | CC(C)N(C)c1nccc(Oc2ccc(NC(=O)c3cc(F)cc(N4CCCCC4)c3)c3ccccc23)n1 | null | null | null |
1,603,426 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[N:18]=[C:17]3I)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:31][Si:32]([C:35]#[CH:36])([CH3:34])[CH3:33]>CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC... | C#C[Si](C)(C)C | CC(C)(C)OC(=O)N1CCC(c2ccc3c(c2)c(I)nn3C(=O)OC(C)(C)C)CC1 | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | 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 | 70 | null | A suspension of tert-butyl 5-[1-(tert-butoxycarbonyl)piperidin-4-yl]-3-iodo-1H-indazole-1-carboxylate (200 mg; 0.38 mmol; 1.0 eq.), (Trimethylsilyl)acetylene (53 μl; 0.38 mmol; 1.0 eq.), TEA (158 μl) and bis(triphenylphosphine)palladium(II) chloride (10.7 mg; 0.02 mmol; 0.04 eq.) was heated at 70° C. overnight in a sea... | CC(C)(C)OC(=O)N1CCC(c2ccc3c(c2)c(C#C[Si](C)(C)C)nn3C(=O)OC(C)(C)C)CC1 | null | 105.7 | null |
1,172,328 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [CH3:1][C:2]1[N:3]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.[N:14]#[C:15][NH2:16].Cl>C(O)C>[CH3:1][C:2]1[N:3]([C:7]2[CH:13]=[CH:12][C:10]([NH:11][C:15]([NH2:16])=[NH:14])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1 | Cc1nccn1-c1ccc(N)cc1 | N#CN | 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 | null | null | To a solution of 4-(2-methyl-1H-imidazol-1-yl)aniline (2 g, 11.55 mmol) in ethanol (25 mL) was added cyanamide (0.728 g, 17.32 mmol) and hydrochloric acid (1.422 mL, 17.32 mmol). The reaction mixture was refluxed for 4 h. An additional 1 eq of hydrochloric acid (1.422 ml, 17.32 mmol) was added and precipitation occurre... | Cc1nccn1-c1ccc(NC(=N)N)cc1 | null | 64.4 | null |
1,406,714 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH:18]([F:20])[F:19])[N:6]2[CH:13]([CH3:17])[C:14]([OH:16])=O.[CH3:21][N:22](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:23].F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CNC>CN(C=O)C>[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH:18](... | CC(C(=O)O)n1c(C(F)F)cc2c(Cl)c(C#N)ccc21 | CN(C)C(On1nnc2cccnc21)=[N+](C)C | null | CNC | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 0.17 | To a solution of 2-[4-chloro-5-cyano-2-(difluoromethyl)-1H-indol-1-yl]propanoic acid (0.010 g, 0.034 mmol) in anhydrous DMF (1.5 mL) was added HATU (0.014 g, 0.037 mmol) and DIEA (0.0048 g, 0.0037 mmol) and stirred at rt. After 10 min, dimethylamine (2M in THF, 0.17 mL, 0.34 mmol) was added and stirred at rt for 45 min... | CC(C(=O)N(C)C)n1c(C(F)F)cc2c(Cl)c(C#N)ccc21 | null | 63.2 | null |
648,319 | ord_dataset-5d77a731aa10488794c824ad12021f57 | null | 2004-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][N:3]=1.[NH2:11][C:12]1[C:13]([Cl:19])=[N:14][CH:15]=[N:16][C:17]=1[Cl:18]>>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([NH:11][C:12]2[C:13]([Cl:19])=[N:14][CH:15]=[N:16][C:17]=2[Cl:18])=[O:7])=[CH:9][CH:10]=1 | O=C(Cl)c1ccc(Cl)nc1 | Nc1c(Cl)ncnc1Cl | null | null | null | null | null | null | null | 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 6-chloronicotinoyl chloride and 5-amino-4,6-dichloropyrimidine as a white solid as described in Example 1. 1H NMR (CDCl3): 8.95 (d, J=2.4, 1H), 8.78 (s, 1H), 8.25-8.22 (m, 1H), 7.57 (s, 1H), 7.54 (d, J=8.4, 1H). | O=C(Nc1c(Cl)ncnc1Cl)c1ccc(Cl)nc1 | null | null | null |
76,596 | ord_dataset-8c94910e81cc4281bd57a58ce657576f | null | 1981-01-01T00:02:00 | true | [Cl:1][C:2]1[C:3](C(O)=O)=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.C(=O)=O>>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1 | CSc1ncc(Cl)c(C(=O)O)n1 | null | null | O=C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 5-Chloro-2-methylthio-4-pyrimidine carboxylic acid (30 g) was heated at 180°-200° C. until all the solid had melted and the evolution of carbon dioxide had ceased (5 min). The residue was allowed to cool and then washed with several portions of chloroform. The chloroform washings were filtered to remove dark insoluble ... | CSc1ncc(Cl)cn1 | null | 89.2 | null |
1,252,994 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [CH2:1]([O:3][C:4](=[O:24])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9](B2OC(C)(C)C(C)(C)O2)[CH:8]=1)[CH3:6])[CH3:2].Br[C:26]1[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][C:27]=1[CH:28]=[O:29]>>[CH2:1]([O:3][C:4](=[O:24])[CH:5]([C:7]1[CH:8]=[C:9]([C:26]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F... | O=Cc1cc(C(F)(F)F)ccc1Br | CCOC(=O)C(C)c1ccc(OC)c(B2OC(C)(C)C(C)(C)O2)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 | Prepared according to the procedure described in Example 1, Step 4, using the following starting materials: 2-[4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid ethyl ester and 2-bromo-5-(trifluoromethyl)benzaldehyde. | CCOC(=O)C(C)c1ccc(OC)c(-c2ccc(C(F)(F)F)cc2C=O)c1 | null | null | null |
517,897 | ord_dataset-a495451286334c5c9bbcbd48a00c1350 | null | 2001-01-01T00:09:00 | true | [NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]>C(O)(=O)C.[Pt](=O)=O>[NH:1]1[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11] | CCOC(=O)c1cc2ccccc2[nH]1 | null | null | O=[Pt]=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | Ethyl indole-2-carboxylate (0.5 g) and platinum (IV) oxide (0.1 g) in acetic acid (20 ml) were stirred under an atmosphere of hydrogen for 16 hours at ambient temperature. The reaction was then filtered through a pad of celite and basified by addition of aqueous sodium hydroxide (2N). The resulting precipitate was filt... | CCOC(=O)c1cc2c([nH]1)CCCC2 | null | 33.3 | null |
1,199,815 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | Cl[C:2]1[N:7]2[N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH:20]1([NH2:27])[CH2:25][CH2:24][CH2:23][CH:22]([NH2:26])[CH2:21]1>>[NH2:26][CH:22]1[CH2:23][CH2:24][CH2:25][CH:20]([NH:27][C:2]2[N:7]3[N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]4[CH:18]=[CH:... | NC1CCCC(N)C1 | O=C(Nc1nc2cccc(Cl)n2n1)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 | 0.08 | The title compound was prepared following procedure described for example 30 but starting from N-(5-chloro[1,2,4]triazolo[1,5-a]pyridin-2-yl)benzamide ((B3), 52 mg; 0.19 mmol; 1.0 eq) and 1,3-cyclohexanediamine (1.0 mL). The crude was directly purified by preparative HPLC (Starting with 45% ACN in water for 5 min, then... | NC1CCCC(Nc2cccc3nc(NC(=O)c4ccccc4)nn23)C1 | null | null | null |
903,712 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [CH3:1][CH:2]([CH3:16])[CH2:3][CH2:4][N:5]1[C:13](=[O:14])O[C:11](=[O:15])[C:10]2[N:6]1[CH:7]=[CH:8][CH:9]=2.C(OCC)(=O)[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].[H-].[Na+]>CN(C)C(=O)C.CO>[CH2:22]([O:21][C:19]([C:18]1[C:13](=[O:14])[N:5]([CH2:4][CH2:3][CH:2]([CH3:1])[CH3:16])[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]2[C:11]=1... | CCOC(=O)CC(=O)OCC | CC(C)CCn1c(=O)oc(=O)c2cccn21 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)N(C)C | CO | null | null | null | null | null | null | null | null | null | 120 | 16 | To a solution of 4-(3-methyl-butyl)-6-oxa-3a,4-diaza-indene-5,7-dione (Example 1e, 0.080 g, 0.36 mmol) and diethyl malonate (0.58 mL, 3.6 mmol) in N,N-dimethylacetamide (1 mL) was added sodium hydride (0.017 g, 0.43 mmol) and 1 drop of methanol. The reaction mixture was heated to 120° C. and stirred for 16 h. The react... | CCOC(=O)c1c(O)c2cccn2n(CCC(C)C)c1=O | null | 55.6 | null |
378,248 | ord_dataset-846d411edee44814931e062174d7ef12 | null | 1997-01-01T00:09:00 | true | C([O:4][CH2:5][C:6]([N:8]1[C:13]2=[C:14]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[C:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[N:16][N:12]2[CH2:11][CH2:10][NH:9]1)=[O:7])(=O)C.[OH-].[Na+]>C(O)C>[F:23][C:20]1[CH:19]=[CH:18][C:17]([C:15]2[C:14]([C:24]3[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=3)=[C:13]3... | CC(=O)OCC(=O)N1NCCn2nc(-c3ccc(F)cc3)c(-c3ccncc3)c21 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2-acetoxyacetyl-7-(4-fluorophenyl)-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine (75 mg, 0.190 mmol) and an aqueous sodium hydroxide solution (1N, 0.38 ml, 0.380 mmol) in ethanol (1.5 ml) was stirred for 30 minutes at ambient temperature. After dilution of an aqueous saturated ammonium ... | O=C(CO)N1NCCn2nc(-c3ccc(F)cc3)c(-c3ccncc3)c21 | null | 29.8 | null |
577,092 | ord_dataset-a9ba4801408c4b01922886164c10a391 | null | 2003-01-01T00:01:00 | true | [N:1]1[C:6]2[CH:7]=[CH:8][S:9][C:5]=2[C:4](=[O:10])[NH:3][CH:2]=1.[Br:11]Br.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[Br:11][C:7]1[C:6]2[N:1]=[CH:2][NH:3][C:4](=[O:10])[C:5]=2[S:9][CH:8]=1 | O=c1[nH]cnc2ccsc12 | BrBr | null | O=C([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 | 25 | null | To a solution of 3H-thieno[3,2-d]pyrimid-4-one (82, 0.98 g, 6.4 mmol) in acetic acid (3.4 mL) was added a solution of bromine (1 mL) in acetic acid (3 mL). The reaction mixture was heated at reflux for 8 hours. The resulting suspension was allowed to cool to room temperature and then poured into a saturated aqueous sol... | O=c1[nH]cnc2c(Br)csc12 | null | 64 | null |
321,369 | ord_dataset-eed8d32c2f1d46a89ba39d04dfaa83b1 | null | 1995-01-01T00:12:00 | true | [NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[CH3:6][C:7]1[C:12](=[O:13])[C:11]2[CH:14]=[CH:15][CH:16]=[C:17]([C:18](Cl)=[O:19])[C:10]=2[O:9][C:8]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>O.CC(C)=O>[OH:5][CH2:4][CH2:3][CH2:2][NH:1][C:18]([C:17]1[C:10]2[O:9][C:8]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:... | NCCCO | Cc1c(-c2ccccc2)oc2c(C(=O)Cl)cccc2c1=O | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | O | null | null | null | null | null | null | null | null | null | null | 3 | A solution of 7.6 ml of 3-aminopropanol in 50 ml of water was added dropwise over a period of 30 minutes to a suspension of 30 g of 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carbonyl chloride and 15.2 g of potassium carbonate in 400 ml of acetone. The thick suspension was stirred for 3 hours at 20°-25° C. The solvents ... | Cc1c(-c2ccccc2)oc2c(C(=O)NCCCO)cccc2c1=O | null | null | null |
1,618,190 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [Na].Br[C:3]1[N:8]=[CH:7][C:6]([C:9]2([C:17]#[N:18])[CH2:14][CH2:13][C:12]([F:16])([F:15])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[CH2:19]([OH:21])[CH3:20]>>[CH2:19]([O:21][C:3]1[N:8]=[CH:7][C:6]([C:9]2([C:17]#[N:18])[CH2:14][CH2:13][C:12]([F:16])([F:15])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)[CH3:20] | N#CC1(c2ccc(Br)nc2)CCC(F)(F)CC1 | CCO | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 70 | null | Sodium metal (229 mg, 9.96 mmol) was added to ethanol (5 mL) at room temperature. To this solution was added 1-(6-bromo-pyridin-3-yl)-4,4-difluoro-cyclohexanecarbonitrile (300 mg, 1.00 mmol) and the reaction was heated at 70° C. for 6 hours. After cooling to room temperature the volatiles were removed under reduced pre... | CCOc1ccc(C2(C#N)CCC(F)(F)CC2)cn1 | null | 49 | null |
999,600 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | Br[C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[O:14]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15]1.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(... | OB(O)c1ccoc1 | Brc1cccc(N2CCNCC2)c1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | O | null | null | null | null | null | null | null | null | null | 25 | null | A mixed solution of 1-(3-bromophenyl)-piperazine (100 mg, 0.415 mmol), 3-furylboronic acid (69.6 mg, 0.622 mmol), tetrakis(triphenylphosphine)palladium (57.5 mg, 0.050 mmol), 2N aqueous solution of sodium carbonate (1.66 ml, 3.32 mmol) in toluene (4.0 ml) was stirred at 95° C. for 14 hours under a nitrogen atmosphere. ... | c1cc(-c2ccoc2)cc(N2CCNCC2)c1 | null | 47.9 | null |
472,617 | ord_dataset-cd531114850e4f239b2a3661044ae672 | null | 2000-01-01T00:08:00 | true | C([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH2:16][CH2:17][OH:18])[C:10]=1[CH3:19])C1C=CC=CC=1>Br>[OH:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH2:16][CH2:17][OH:18])[C:10]=1[CH3:19] | Cc1c(OCc2ccccc2)c(=O)ccn1CCO | null | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 3-Benzyloxy-1-(2'-hydroxyethyl)-2-methylpyrid-4-one (2 g) is added to concentrated hydrobromic acid (10 ml) and the mixture is heated on a steam bath for 30 minutes. The resultant product is then recrystallised from water to yield 3-hydroxy-1(2'-hydroxyethyl)-2-methylpyrid-4-one as white crystals (0.8 g), m.p. 164°-165... | Cc1c(O)c(=O)ccn1CCO | null | 61.3 | null |
1,145,620 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:21])[F:20])[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[CH2:23]1OC(O)C[O:25][CH:24]1O.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO.C(O)(=O)C>[OH:25][CH2:24][CH2:23][NH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[CH:18... | OC1COC(O)CO1 | Nc1ccc2cc(-c3ccccc3C(F)(F)F)[nH]c(=O)c2c1 | null | O=C([O-])O | [BH3-]C#N | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | CO | null | null | null | null | null | null | null | null | null | 25 | 8 | 350 mg (1.15 mmol) of the 7-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one obtained in Example 38 was dissolved in 11.5 ml of methanol, and thereafter, 1.15 ml of acetic acid and 552.5 mg (4.60 mmol) of glycolaldehyde dimer were added thereto. Thereafter, 722 mg (11.5 mmol) of sodium cyanoborohydride was added ... | O=c1[nH]c(-c2ccccc2C(F)(F)F)cc2ccc(NCCO)cc12 | null | 15.4 | null |
1,651,841 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [CH:1]1([NH:5][C:6]2[N:7]=[N:8][C:9]([C:12]#[CH:13])=[CH:10][CH:11]=2)[CH2:4][CH2:3][CH2:2]1.I[C:15]1[CH:16]=[C:17]([CH:37]=[CH:38][C:39]=1[CH3:40])[C:18]([NH:20][C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([N:31]2[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]2)[CH:22]=1)=[O:19]>>[CH:1]1([NH:5][C:6]2[N:7]=... | C#Cc1ccc(NC2CCC2)nn1 | Cc1cn(-c2cc(NC(=O)c3ccc(C)c(I)c3)cc(C(F)(F)F)c2)cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was synthesized from N-cyclobutyl-6-ethynylpyridazin-3-amine and 3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide (as prepared above) in a manner similar to that described for in Example 1. The product was obtained as a pale yellow solid. Mp: 223-225° C.; 1H NMR (3... | Cc1cn(-c2cc(NC(=O)c3ccc(C)c(C#Cc4ccc(NC5CCC5)nn4)c3)cc(C(F)(F)F)c2)cn1 | null | null | null |
1,496,643 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [CH3:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH:10]2[N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17][C:12]3([CH2:16][CH2:15][CH2:14][CH2:13]3)[CH2:11]2)[CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:13]1[C:12]2([CH2:17][CH2:18][NH:19][CH:10]([CH2:9][NH:8][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=3)[CH2:11]2)[CH2:16][CH2:15][CH2:1... | Cc1cccc(NCC2CC3(CCCC3)CCN2C(=O)OC(C)(C)C)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 0 | 1 | (±)tert-butyl 7-(((6-methylpyridin-2-yl)amino)methyl)-8-azaspiro[4.5]decane-8-carboxylate (intermediate 73, 1.3 g, 3.62 mmol) was dissolved in dichloromethane (10 ml) and cooled to 0° C., then trifluoroacetic acid (30 ml) was added. After 1 hour at 0° C. and 2 hours at room temperature the solution was evaporated, the ... | Cc1cccc(NCC2CC3(CCCC3)CCN2)n1 | null | 95.8 | null |
414,172 | ord_dataset-275344fd078b4340b89ca0b6e92beb95 | null | 1998-01-01T00:10:00 | true | [CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N:13]2[CH:17]=[CH:16][CH:15]=[CH:14]2)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=O.[NH2:18][CH2:19][CH2:20][OH:21].[BH4-].[Na+].C(=O)([O-])O.[Na+]>CO>[OH:21][CH2:20][CH2:19][NH:18][CH2:1][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N:13]2[CH:17]=[CH:16][CH:15]=[CH:14]2)[CH:12]=1)[C:6]([O:8][CH... | COC(=O)c1cc(C=O)cc(-n2cccc2)c1 | NCCO | null | O=C([O-])O | [BH4-] | [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 | 25 | 6 | A mixture of methyl 3-formyl-5-(pyrrol-1-yl)benzoate (1.66 g), 2-aminoethanol (0.88 ml) and molecular sieves 4A (1.7 g) in methanol (40 ml) was stirred for 6 hours at room temperature. Then, to the reaction mixture was added sodium borohydride (0.55 g). After stirring for 3 hours at room temperature, the reaction mixtu... | COC(=O)c1cc(CNCCO)cc(-n2cccc2)c1 | null | null | null |
723,143 | ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | null | 2006-01-01T00:08:00 | true | Br[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:11]2[C:15]3[S:16][CH:17]=[CH:18][C:14]=3[O:13][N:12]=2)[CH:8]=[CH:9][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>C(#N)C>[N:25]1([CH2:2][CH2:3][O:4][C:5]2[CH:6]=[C:7]([C:11]3[C:15]4[S:16][CH:17]=[CH:18][C:14]=4[O:13][N:12]=3)[CH:8]=[CH:9][CH:10]... | BrCCOc1cccc(-c2noc3ccsc23)c1 | C1CCNC1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, pyrrolidine and acetonitrile essentially as described above in example 40. Purity by LC/MS (APCI)=100%, [M+H]+=315. | c1cc(OCCN2CCCC2)cc(-c2noc3ccsc23)c1 | null | null | null |
664,882 | ord_dataset-5a3d853c53674888a5691dce2e398792 | null | 2005-01-01T00:03:00 | true | [C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]([CH2:18]OS(C)(=O)=O)[C:10](=[O:17])[N:11]([CH2:13][CH:14]([CH3:16])[CH3:15])[N:12]=2)=[CH:3][CH:2]=1.[CH3:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>>[C:1]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:6]=[CH:5][C:... | CC(C)Cn1nc(-c2ccc(-c3ccccc3)cc2)cc(COS(C)(=O)=O)c1=O | CN1CCNCC1 | null | null | null | null | null | null | null | 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 of Example 1(10), 6-(4-biphenylyl)-2-isobutyl-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and 1-methylpiperazine were reacted to yield the title compound as a yellow oil (yield: 68.2%). | CC(C)Cn1nc(-c2ccc(-c3ccccc3)cc2)cc(CN2CCN(C)CC2)c1=O | null | 68.2 | null |
1,196,508 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH2:9][CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:4][CH:3]=1.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:21]2[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=2)[CH2:9][CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:4][CH... | Clc1ccccc1 | OC(CCn1ccnc1)c1ccc(Br)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 | Chlorobenzene (5 ml) was reacted with 1-(4-Bromo-phenyl)-3-imidazol-1-yl-propan-1-ol (0.41 mg, 1.46 mmol) following the procedure set out in Example 42B to give the title compound (0.37 g, 67% yield). LC/MS: (PS-A2) Rt 2.40 [M+H]+ 375.16, 377.17. | Clc1ccc(C(CCn2ccnc2)c2ccc(Br)cc2)cc1 | null | 67 | null |
220,928 | ord_dataset-42629b4cf1094978a5e5f29f22639ee7 | null | 1991-01-01T00:01:00 | true | Cl.Cl.[NH2:3][CH:4]1[CH:9]2[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]2)[CH2:5]1.[F:12][C:13]([F:27])([F:26])[C:14]1[CH:15]=[C:16]([CH:23]=[CH:24][CH:25]=1)[C:17]([NH:19][C:20](N)=[O:21])=[O:18].C(N(C(C)C)CC)(C)C>N1C=CC=CC=1>[N:6]12[CH2:11][CH2:10][CH:9]([CH2:8][CH2:7]1)[CH:4]([NH:3][C:20]([NH:19][C:17](=[O:18])[C:16]1[CH:23]... | NC1CN2CCC1CC2 | NC(=O)NC(=O)c1cccc(C(F)(F)F)c1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | The above compound was prepared from 3-amino quinuclidine dihydrochloride (1.0 g, 5 mmol), 3-trifluoromethylbenzoylurea (1.16 g, 5 mmol) and diisopropylethylamine (1.29 g, 10 mmol) in pyridine (20 ml), by refluxing under nitrogen overnight. The solvent was evaporated and the residue worked-up as in Example 1. The produ... | O=C(NC(=O)c1cccc(C(F)(F)F)c1)NC1CN2CCC1CC2 | null | null | null |
534,189 | ord_dataset-b1a34bc8c1204d51a772ed27396c794e | null | 2002-01-01T00:02:00 | true | [NH:1]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].O[N:21]1[C:25](=[O:26])[CH2:24][CH2:23][C:22]1=[O:27].C1CCC(N=C=NC2CCCCC2)CC1>O1CCOCC1>[NH:1]([C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11])[C@H:2]([... | O=C1CCC(=O)N1O | CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)O | null | C(=NC1CCCCC1)=NC1CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 0 | 0.5 | Z-Leu-OH (15.92 g) and N-hydroxysuccinimide (6.9 g) were dissolved in dioxane and cooled to 0° C. To the cooled solution, DCC was added and stirred at 0° C. for 0.5 h, then room temp overnight. After filtering off the byproduct urea, the filtrate was concentrated to give crude Z-Leu-OSu as an oil. | CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)ON1C(=O)CCC1=O | null | null | null |
1,541,671 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[C:5]([C:14]2[C:15]([F:39])=[C:16]([N:21](COCCOC)[S:22]([C:25]3[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=3[F:32])(=[O:24])=[O:23])[CH:17]=[CH:18][C:19]=2[F:20])=[N:4]1)[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.C([NH2:55])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2... | CC(C)(C)N | CCn1cc(-c2ccncc2)c(-c2c(F)ccc(N(COCCOC)S(=O)(=O)c3cc(F)ccc3F)c2F)n1 | null | O=C(OO)c1cccc(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 3 | N-[3-(1-ethyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluoro-N-(2-methoxy-ethoxymethyl)-benzenesulfonamide (123 mg, 0.217 mmol) was dissolved in dry DCM, mCPBA (75 mg, 2 eq) was added and the reaction mixture was stirred at room temperature for 3 hours. A further addition of mCPBA was made (50 mg) an... | CCn1cc(-c2ccnc(N)c2)c(-c2c(F)ccc(NS(=O)(=O)c3cc(F)ccc3F)c2F)n1 | null | 43.1 | null |
346,041 | ord_dataset-d0003732f14e4648a00d341275654590 | null | 1996-01-01T00:11:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:26])[C:11]2[CH:16]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:14]([OH:21])=[C:13]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:12]=2)=[C:5]([N+:27]([O-])=O)[CH:4]=1>C(O)C.[Pd]>[NH2:27][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[NH:9][C:10](=[O:26])[C:11]1[CH:16... | COc1ccc(NC(=O)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)c([N+](=O)[O-])c1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of N-(4-methoxy-2-nitrophenyl)-3,5-di-t-butyl-4-hydroxybenzamide (1.50 g) in ethanol (10 ml) was added a catalytic amount of 10% palladium/carbon to perform catalytic reduction under a pressure of 1-2.5 arms at room temperature for 5 hrs. After filtering the catalyst and distilling off the solvent, crysta... | COc1ccc(NC(=O)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)c(N)c1 | null | 56.9 | null |
635,854 | ord_dataset-de283386b8034acd99fba96d3c7d3227 | null | 2004-01-01T00:04:00 | true | [CH3:1][CH:2]([CH3:32])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24](=O)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:14][CH2:13]2)[CH:7]=1)=[O:4].Cl.[F:34][C:35]([F:46])([F:45])[O:36][C:37]1[CH:42]=[CH:41][C:40]([NH:43]N)=[CH:3... | CC(C)C(=O)Nc1cccc(C2CCN(CCCCCCC(=O)c3ccccc3)CC2)c1 | NNc1ccc(OC(F)(F)F)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 | Prepared by Procedure E and Scheme M using 2-methyl-N-{3-[1-(7-oxo-7-phenylheptyl)-4-piperidinyl]phenyl}propanamide and 1-[4-(trifluoromethoxy)phenyl]hydrazine hydrochloride: ESMS m/e: 592.3 (M+H)+. | CC(C)C(=O)Nc1cccc(C2CCN(CCCCCc3c(-c4ccccc4)[nH]c4ccc(OC(F)(F)F)cc34)CC2)c1 | null | null | null |
1,219,724 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [CH3:1][N:2]([CH3:14])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][CH2:7][CH2:6]2.C(=O)([O-])[O-].[K+].[K+].CS(C)=O.[Br:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28](Br)[C:27]=1[CH3:33]>ClCCl>[Br:25][C:26]1[C:27]([CH3:33])=[C:28]([N:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([N:2]([CH3:14])[CH3:1... | CN(C)c1ccc2c(c1)CCNC2=O | Cc1c(Br)cccc1Br | null | O=C([O-])[O-] | [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 | 150 | null | 6-Dimethylamino-3,4-dihydro-2H-isoquinolin-1-one (150 mg, 0.789 mmol), cuprous iodide (30 mg, 0.16 mmol) and potassium carbonate (109 mg, 0.789 mmol) were deposited in a sealed vessel. 3 mL DMSO and 2,6-dibromotoluene (395 mg, 1.58 mmol) were added. Argon was bubbled through the mixture for 2 minutes and the lid was ti... | Cc1c(Br)cccc1N1CCc2cc(N(C)C)ccc2C1=O | null | 63.9 | null |
1,184,177 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[CH:10]1([CH:16]=[CH:17][C:18](Cl)=O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:18]([CH:17]=[CH:16][CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)=[N:9][C:4]=2[CH:3]=1 | O=C(Cl)C=CC1CCCCC1 | Nc1ccc(Br)cc1N | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 40 | 6 | To a solution of 4-bromo-benzene-1,2-diamine (3.0 g, 16.1 mmol) in anhydrous toluene (50 ml) was added a solution of 3-cyclohexyl-acryloyl chloride (as prepared in STEP B above, 32.5 mmol) in toluene (5 ml). The resulting solution was stirred at 40° C. for 6 h. To the resulting solution was added p-toluenesulfonic acid... | Brc1ccc2[nH]c(C=CC3CCCCC3)nc2c1 | null | null | null |
1,446,210 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7]([C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:9]=2)[NH:4][C:3]1=O.P(Cl)(Cl)([Cl:20])=O.C(N(CC)C1C=CC=CC=1)C.P(Cl)(Cl)(Cl)(Cl)Cl>>[Cl:20][C:3]1[N:2]([CH3:1])[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7]([C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:9]=2)[N:4]=1 | O=P(Cl)(Cl)Cl | COC(=O)c1ccc2c(=O)n(C)c(=O)[nH]c2c1 | null | ClP(Cl)(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | 120 | 24 | Into a round bottom flask was added methyl 3-methyl-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate (0.48 g, 2.1 mmol) dissolved in phosphoryl chloride (20.0 mL, 214 mmol). N,N-diethylaniline (0.99 mL, 6.2 mmol) was added followed by phosphorus pentachloride (0.22 g, 1.05 mmol). The reaction mixture was heated to... | COC(=O)c1ccc2c(=O)n(C)c(Cl)nc2c1 | null | 22.6 | null |
1,392,579 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[CH3:14][N:15]1[C:19]([NH2:20])=[CH:18][CH:17]=[N:16]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:14][N:15]1[C:19]([NH:20][C:7](=[O:8])[C:6]2[CH:10]=[CH:11][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=2)=[CH:18][CH:17]=[N:16]1 | O=C(Cl)c1ccc(C(F)(F)F)cc1 | Cn1nccc1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 2 | Under cooling in an ice bath, 4-(trifluoromethyl)benzoyl chloride (8.26 g) was added dropwise to a chloroform (35 mL) solution that contained 1-methyl-1H-pyrazol-5-amine (3.50 g) and triethylamine (5.50 mL), and the obtained solution was then stirred for 2 hours. Thereafter, the reaction solution was diluted with chlor... | Cn1nccc1NC(=O)c1ccc(C(F)(F)F)cc1 | null | 69.6 | null |
445,736 | ord_dataset-a4f0b79f6b9847168861270b79f84afa | null | 1999-01-01T00:11:00 | true | [S:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]([OH:9])=O)=[CH:2]1.Cl.CN(C)CCCN=C=NCC.[O:22]=[C:23]([CH3:33])[CH2:24][NH:25][C:26]([CH3:32])([CH3:31])[C:27]([O:29][CH3:30])=[O:28]>ClCCl>[O:22]=[C:23]([CH3:33])[CH2:24][N:25]([C:7](=[O:9])[CH2:6][C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)[C:26]([CH3:32])([CH3:31])[C:27]([O:29][CH3:30])=[O:2... | O=C(O)Cc1ccsc1 | COC(=O)C(C)(C)NCC(C)=O | null | CCN=C=NCCCN(C)C | Cl | 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 | 0.17 | To a solution of thiophen-3-acetic acid (8.7 g) in dichloromethane (70 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (11.7 g), and the mixture was stirred for 10 minutes at room temperature. To the solution was added dropwise a solution of methyl 2-(2-oxopropylamino)isobutyrate (10.6 g) in d... | COC(=O)C(C)(C)N(CC(C)=O)C(=O)Cc1ccsc1 | null | 41.8 | null |
326,014 | ord_dataset-8fe3c7256e6747e59933c880f5f642a0 | null | 1996-01-01T00:03:00 | true | [C:1]([S:4][CH2:5][CH:6]([CH2:10][CH:11]([CH3:13])[CH3:12])[C:7](Cl)=[O:8])(=[O:3])[CH3:2].[NH2:14][C@H:15]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:1]([S:4][CH2:5][CH:6]([CH2:10][CH:11]([CH3:13])[CH3:12])[C:7]([NH:14][C@H:15]([C:23]([O:25... | CCOC(=O)[C@@H](N)Cc1ccccc1 | CC(=O)SCC(CC(C)C)C(=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 | null | 2-Acetylthiomethyl-4-methylpentanoyl chloride and (L)-phenylalanine, ethyl ester are reacted in methylene chloride in the presence of diisopropylethylamine at a temperature below 0° according to the procedure of Example 26 to yield (±)-N-[2-(acetylthiomethyl)-4-methyl-1-oxopentyl]-L-phenylalanine, ethyl ester as an off... | CCOC(=O)[C@H](Cc1ccccc1)NC(=O)C(CSC(C)=O)CC(C)C | null | null | null |
1,147,896 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | C([O:8][C:9]1[CH:10]=[C:11]([CH:27]=[CH:28][CH:29]=1)[CH2:12][N:13]([C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=1)[N:14]1[CH:18]=[N:17][N:16]=[CH:15]1)C1C=CC=CC=1>C1COCC1.CO.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:27]=[CH:28][CH:29]=1)[CH2:12][N:13]([C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=... | N#Cc1ccc(N(Cc2cccc(OCc3ccccc3)c2)n2cnnc2)cc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 16 | To a solution of 4-[(3-Benzyloxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole (0.4 g, 1.05 mmol) in anhydrous THF/MeOH (20 mL) was added Pd—C (10% by wt., 0.04 g). The black suspension was then stirred under an atmosphere of hydrogen (balloon) for 16 h. The catalyst was removed by filteration through Celite® and exha... | N#Cc1ccc(N(Cc2cccc(O)c2)n2cnnc2)cc1 | null | 88.3 | null |
1,051,901 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [CH2:1]([C:7]1[CH:8]=[C:9]([C:13]2[N:17]([CH3:18])[C:16]([C:19]([N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[CH2:31][CH2:30][CH2:29][C@@H:28]4[CH2:32][OH:33])[CH2:23][CH2:22]3)=[O:20])=[C:15](I)[N:14]=2)[CH:10]=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[N:35]1[CH:40]=[C:39](B(O)O)[CH:38]=[N:37][CH:36]=1>>[CH2:1]([... | OB(O)c1cncnc1 | CCCCCCc1cccc(-c2nc(I)c(C(=O)N3CCC(N4CCC[C@@H]4CO)CC3)n2C)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 | In analogy to the procedure described for example 7, [2-(3-hexyl-phenyl)-5-iodo-3-methyl-3H-imidazol-4-yl]-[4-((R)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-methanone (example 45) was reacted with pyrimidine-5-yl-boronic acid to give the title compound as light yellow oil. MS: 531.3 (MH+). | CCCCCCc1cccc(-c2nc(-c3cncnc3)c(C(=O)N3CCC(N4CCC[C@@H]4CO)CC3)n2C)c1 | null | null | null |
1,221,278 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | Br[C:2]1[Se:3][CH:4]=[CH:5][CH:6]=1.[F:7][C:8]1[C:13]([F:14])=[C:12]([O:15][CH2:16][CH2:17][CH3:18])[CH:11]=[CH:10][C:9]=1[C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.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... | Brc1ccc[se]1 | CCCOc1ccc(-c2ccc(B(O)O)cc2)c(F)c1F | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | A mixture of 12.7 g (60.6 mmol) of 2-bromoselenophene, 17.7 g (60.6 mmol) of 2′,3′-difluoro-4′-propoxybiphenyl-4-ylboronic acid, 5.55 g (4.80 mmol) of tetrakis(triphenylphosphine)palladium(0) and 180 ml of 2 N sodium carbonate soln. in 600 ml of toluene/ethanol (1:1) is heated under reflux for 20 h. After cooling, the ... | CCCOc1ccc(-c2ccc(-c3ccc[se]3)cc2)c(F)c1F | null | null | null |
1,572,734 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | Cl.[S:2]1[C:6]2[CH2:7][CH2:8][CH2:9][C:5]=2[N:4]=[C:3]1[NH2:10].[C:11]12([C:21](Cl)=[O:22])[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C1COCC1>[S:2]1[C:6]2[CH2:7][CH2:8][CH2:9][C:5]=2[N:4]=[C:3]1[NH:10][C:21]([C:11]12[CH2:20][CH:15]3[CH2:14][CH:13]([CH2:19]... | O=C(Cl)C12CC3CC(CC(C3)C1)C2 | Nc1nc2c(s1)CCC2 | null | CN(C)c1ccncc1 | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | A mixture of 5,6-dihydro-4H-cyclopentathiazole-2-ylamine hydrochloride (400 mg, 2.27 mmol), 1-adamantanecarbonyl chloride (540 mg, 2.72 mmol), 4-dimethylaminopyridine (100 mg, 0.82 mmol) and triethylamine (632 μL, 4.54 mmol) in 30 mL of THF was processed according to the method of Example 1A to afford the title compoun... | O=C(Nc1nc2c(s1)CCC2)C12CC3CC(CC(C3)C1)C2 | null | null | null |
236,879 | ord_dataset-56e7a343b17a4d6da818127ceb19589d | null | 1991-01-01T00:11:00 | true | [OH:1][C@H:2]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:3][C@@H:4]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[C:5]#[N:6].[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.Cl>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27]([O:1][C@... | CCCCCC[C@@H](O)C[C@H](C#N)c1ccc(OC)cc1 | Cc1ccc(S(=O)(=O)Cl)cc1 | null | CN(C)c1ccncc1 | Cl | 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 | 72 | To a solution of 559 mg (2.0 mmol) of (2S,4R)-4-hydroxy-2-(4-methoxyphenyl)decanenitrile in 5 ml of pyridine were added, with cooling with ice, a solution of 774 mg (4.1 mmol) of p-toluenesulfonyl chloride (TsCl) in 3 ml of pyridine and 24 mg (0.2 mmol) of 4-(N,N-dimethylamino)pyridine (DMAP). This mixture was stirred ... | CCCCCC[C@H](C[C@H](C#N)c1ccc(OC)cc1)OS(=O)(=O)c1ccc(C)cc1 | null | 64 | null |
346,595 | ord_dataset-d0003732f14e4648a00d341275654590 | null | 1996-01-01T00:11:00 | true | [ClH:1].[NH2:2][CH:3]([CH2:23][O:24][CH3:25])[CH2:4][O:5][C:6]1[C:10]2[CH:11]=[C:12]([O:15]CC3C=CC=CC=3)[CH:13]=[CH:14][C:9]=2[O:8][N:7]=1>CO.[C].[Pd]>[ClH:1].[NH2:2][CH:3]([CH2:23][O:24][CH3:25])[CH2:4][O:5][C:6]1[C:10]2[CH:11]=[C:12]([OH:15])[CH:13]=[CH:14][C:9]=2[O:8][N:7]=1 | COCC(N)COc1noc2ccc(OCc3ccccc3)cc12 | null | null | [Pd] | Cl | 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 suspension of 0.40 g of 3-(2-amino-3-methoxypropoxy)-5-benzyloxy-1,2-benzoisoxazole hydrochloride in 20 ml of methanol is added 0.1 g of 5% palladium carbon, and they are subjected to catalytic reduction at 20°-25° C. under atmospheric pressure. The 5% palladium carbon is removed from the reaction mixture by filtr... | COCC(N)COc1noc2ccc(O)cc12 | null | null | null |
686,540 | ord_dataset-56747de2718a4ac5bf061651d1cc9e3e | null | 2005-01-01T00:10:00 | true | [CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:5]=2[S:4][N:3]=1.[Br:12][CH2:13][CH2:14][CH:15](Br)[CH3:16]>>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][O:11][C:9]1[CH:8]=[CH:7][C:6]2[C:2]([CH3:1])=[N:3][S:4][C:5]=2[CH:10]=1 | CC(Br)CCBr | Cc1nsc2cc(O)ccc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to example 2.1, 3-Methyl-benzo[d]isothiazol-6-ol and 1,3-dibromobutane were converted to yield 6-(4-Bromo-butoxy)-3-methyl-benzo[d]isothiazole as brown oil, MS: 300 (MH+, 1 Br). | Cc1nsc2cc(OCCCCBr)ccc12 | null | null | null |
1,760,159 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [C:1]1([C:7](=[N:14][CH:15]([CH2:18][CH2:19][F:20])[C:16]#[N:17])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:21]([Li])CCC.IC>C1COCC1>[C:1]1([C:7](=[N:14][C:15]([CH3:21])([CH2:18][CH2:19][F:20])[C:16]#[N:17])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][... | [Li]CCCC | N#CC(CCF)N=C(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CI | C1CCOC1 | null | null | null | null | null | null | null | null | null | -78 | 0.17 | 19.94 g (63.64 mmol, 85% purity) of rac-2-[(diphenylmethylene)amino]-4-fluorobutanonitrile from Example 66A were initially charged in 421 ml of abs. THF, and 25.71 ml (64.28 mmol) of n-butyllithium (2.5 N in hexane) were added at −78° C. under argon, and the mixture was stirred at −78° C. for a further 10 min. Subseque... | CC(C#N)(CCF)N=C(c1ccccc1)c1ccccc1 | null | 96.4 | null |
1,568,357 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[F:21])=O.[NH2:22][C:23]([NH2:25])=[S:24]>CCO>[F:21][C:6]1[CH:7]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH:9]=[C:10]([CH3:11])[C:5]=1[C:3]1[N:22]=[C:23]... | NC(N)=S | COc1ccc(Oc2cc(C)c(C(=O)CBr)c(F)c2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2-bromo-1-(2-fluoro-4-(4-methoxyphenoxy)-6-methylphenyl)ethanone (30-6, 0.60 g) and thiourea (0.160 mg, 2.05 mmol) in 95% EtOH (12.0 mL) was heated at reflux for 60 min. The solution was concentrated under reduced pressure, and the residue was re-dissolved in ethyl acetate. The solution was washed with sat... | COc1ccc(Oc2cc(C)c(-c3csc(N)n3)c(F)c2)cc1 | null | 80.1 | null |
823,640 | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | null | 2008-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH2:13][CH3:14])[N:6]=[C:5]2O.P(Cl)(Cl)([Cl:18])=O.C(N(CC)CC)C>C(Cl)Cl>[Cl:18][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]=[C:7]([CH2:12][CH2:13][CH3:14])[N:6]=1 | CCCc1nc(O)c2cc(Cl)ccc2n1 | O=P(Cl)(Cl)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 | null | null | Preparation D10, Step 3: 6-Chloro-2-propylquinazolin-4-ol (810 mg, 3.64 mmol, 1 eq), phosphorus oxychloride (3.30 mL, 35.1 mmol, 9.64 eq) and triethylamine (1.63 mL, 11.7 mmol, 3.21 eq) were mixed at room temperature then refluxed for 2.5 hours. The reaction was stripped 3 times from methylene chloride. The residue was... | CCCc1nc(Cl)c2cc(Cl)ccc2n1 | null | 58.1 | null |
731,376 | ord_dataset-eb4226b4f7644a01a737e7547b70014a | null | 2006-01-01T00:09:00 | true | C([Li])CCC.C[Si]([C:10]#[CH:11])(C)C.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH2:22][C:21](=[O:25])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[Cl-].N>O1CCCC1.CCCCCC>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH2:22][C:21]([C:10]#[CH:11])([OH:25])[CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14] | CC(C)(C)OC(=O)N1CCCC(=O)C1 | C#C[Si](C)(C)C | null | N | [Cl-] | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCCCCC | null | null | null | null | null | null | null | null | null | null | 1 | In a dry ice-acetone bath, 40 ml of a 1.6 M hexane solution of n-butyllithium was added dropwise to a solution of 6.07 g of trimethylsilylacetylene in 100 ml of tetrahydrofuran. After the temperature was once elevated to 0° C., the mixture was cooled again in a dry ice-acetone bath and a solution of 5.97 g of 1-tert-bu... | C#CC1(O)CCCN(C(=O)OC(C)(C)C)C1 | null | 71.1 | null |
465,172 | ord_dataset-6c36eb0f817d4144988b8963c5d58879 | null | 2000-01-01T00:05:00 | true | [CH2:1]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([C:22]([OH:24])=[O:23])=[C:15]([CH3:21])[C:16]=2[N+:18]([O-:20])=[O:19])[CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].S(=O)(=O)(O)O.[CH3:30]O>>[CH2:1]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([C:22]([O:24][CH3:30])=[O:23])=[C:15]([CH3:21])[C:16]=2[N+:18]([O-:20... | CO | CCCCCCCCN1CCc2cc(C(=O)O)c(C)c([N+](=O)[O-])c21 | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 1-Octyl-5-carboxy-6-methyl-7-nitroindoline (1.4 g) was dissolved in methanol (30 ml), and conc. sulfuric acid (4.1 g) was added, which was followed by refluxing for 4 hr. Methanol was evaporated under reduced pressure. Ethyl acetate (100 ml) was added to the residue. The mixture was washed with water and dried over anh... | CCCCCCCCN1CCc2cc(C(=O)OC)c(C)c([N+](=O)[O-])c21 | null | null | null |
512,364 | ord_dataset-85c00026681b46f89ef8634d2b8618c3 | null | 2001-01-01T00:07:00 | true | [CH:1]([C@@H:3]1[C@@H:7]([C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)[CH2:6][N:5]([C@H:13]([CH2:26][CH:27]2[CH2:30][CH2:29][CH2:28]2)[C:14]([O:16]CC2C=CC(OC)=CC=2)=[O:15])[CH2:4]1)=O.[F:31][C:32]1[CH:33]=[C:34]([CH2:39][CH2:40][CH2:41][CH:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)[CH:35]=[CH:36][C:37]=1[F:38].Cl>>[F:31][C:3... | COc1ccc(COC(=O)[C@@H](CC2CCC2)N2C[C@H](c3ccsc3)[C@@H](C=O)C2)cc1 | Fc1ccc(CCCC2CCNCC2)cc1F | 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 | The title compound was prepared from 21 mg (0.046 mmol) of 2-(R)-(3-(R)-formyl-4-(S)-(3-thienyl)pyrrolidin-1-yl)-3-(cyclobutyl) propanoic acid, (4-methoxy)benzyl ester (from EXAMPLE 87, Step F) and 11.7 mg (0.046 mmol) of 4-(3-(3,4-difluorophenyl)propyl)piperidine.HCl (from EXAMPLE 119, Step C) using procedures analogo... | O=C(O)[C@@H](CC1CCC1)N1C[C@H](CN2CCC(CCCc3ccc(F)c(F)c3)CC2)[C@@H](c2ccsc2)C1 | null | 65.1 | null |
1,219,791 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | F[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.Cl.[NH:13]1[CH2:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[N:13]1([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[C:7](=[O:11])[CH2:6][CH2:5]3)[CH2:16][CH2:15][CH2:14]1 | O=C1CCc2cc(F)ccc21 | C1CNC1 | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 100 | null | 5-fluoro-1-indanone (7.44 g, 49.5 mmol), Azetidine HCl (5.1 g, 54.4 mmol) and K2CO3 (13.6 g, 99 mmol) were taken up in 60 ml of DMSO. The reaction mixture was heated at 100° C. for 6 hours. | O=C1CCc2cc(N3CCC3)ccc21 | null | null | null |
806,337 | ord_dataset-da49b0378abf41bf92ab8ecdd3feb28b | null | 2008-01-01T00:02:00 | true | [CH3:1][O:2][C:3](=[O:28])[CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][C@@H:11]1/[CH:17]=[CH:18]/[CH:19]([OH:27])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[H][H]>[Pd].CO>[CH3:1][O:2][C:3](=[O:28])[CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[CH2:14... | [H][H] | COC(=O)COCCCCN1C(=O)CCC[C@@H]1/C=C/C(O)Cc1ccccc1 | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 4 | Palladium on carbon (10 wt. %, 3 mg) was added to a solution of {4-[(R)-2-((E)-3-hydroxy-4-phenyl-but-1-enyl)-6-oxo-piperidin-1-yl]-butoxy}-acetic acid methyl ester (9.5 mg, 0.024 mmol) in MeOH (2.0 mL). A hydrogen atmosphere was established by evacuating and refilling with hydrogen (3×) and the reaction mixture was st... | COC(=O)COCCCCN1C(=O)CCC[C@@H]1CCC(O)Cc1ccccc1 | null | 87.3 | null |
21,790 | ord_dataset-39f318aa6ec5450182abaf3662294306 | null | 1977-01-01T00:03:00 | true | N([O-])=O.[Na+].N[C:6]1[C:7]([OH:13])=[N:8][CH:9]=[CH:10][C:11]=1[CH3:12].[ClH:14]>O.S>[Cl:14][C:6]1[C:7]([OH:13])=[N:8][CH:9]=[CH:10][C:11]=1[CH3:12] | Cc1ccnc(O)c1N | Cl | null | O=N[O-] | S | [Na+] | 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 | A solution sodium nitrite (2.38 g) in water (10 ml) was added dropwise to a stirred mixture of 3-amino-2-hydroxy-methylpyridine (4.8 g) in aqueous hydrochloric acid (48% 10 ml) and water (5 ml) at 0°-5° C. This solution of the diazonium salt was added to a hot solution of cuprous chloride (2.5 g) in conc. hydrochloric ... | Cc1ccnc(O)c1Cl | null | null | null |
88 | ord_dataset-a0eff6fe4b4143f284f0fc5ac503acad | null | 1976-01-01T00:01:00 | true | F[B-](F)(F)F.[C:6]([N+:10]1[O:11][C:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=12)([CH3:9])([CH3:8])[CH3:7].[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>>[C:6]([N:10]1[C:14]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:13]=2[C:12]([N:26]2[CH2:31][CH2:30][O:29]... | CC(C)(C)[n+]1oc(-c2ccccc2)c2cc(Cl)ccc21 | C1COCCN1 | null | F[B-](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 | 1 | To a flask containing 6 g. of 1-tert.-butyl-5-chloro-3-phenyl-2,1-benzisoxazolium tetrafluoroborate is added 9 ml. of morpholine and the mixture heated at 80°C. with stirring for 1 hour. The reaction mixture is washed in diethyl ether and water and the ether layer separated, dried, evaporated in vacuo to dryness and th... | CC(C)(C)N1OC(c2ccccc2)(N2CCOCC2)c2cc(Cl)ccc21 | null | null | null |
1,577,773 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.Cl[C:12]1[N:17]=[C:16](Cl)[C:15]([F:19])=[CH:14][N:13]=1>CO.O>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([NH:1][C:12]2[N:17]=[C:16]([NH:1][C:2]3[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=3)[C:15]([F:19])=[CH:14][N:13]=2)=[CH:3][CH:4]=1)([OH:8])=[O:7] | Fc1cnc(Cl)nc1Cl | Nc1ccc(C(=O)O)cc1 | null | null | null | 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 | 100 | 24 | A mixture of 4-Aminobenzoic acid (410 mg, 3 mmol) and 2,4-dichloro-5-fluoropyrimidine (100 mg, 0.6 mmol) in methanol (10 mL) and water (1 mL) was stirred at 100° C. for 24 h to yield N2,N4-bis(4-carboxyphenyl)-5-fluoro-2,4-pyrimidinediamine after methanol was removal. This residue was redissolved in DMF (10 mL) and to ... | O=C(O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)O)cc3)n2)cc1 | null | null | null |
125,541 | ord_dataset-fd44e5eeeeb4473cb5fbff2d885d7833 | null | 1985-01-01T00:01:00 | true | [CH2:1]([SH:3])[CH3:2].[H-].[Na+].[F:6][C:7]1[N:8]([C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:9]=[C:10]([CH2:12][CH2:13][CH2:14]OS(C)(=O)=O)[N:11]=1>CN(C=O)C>[CH2:1]([S:3][CH2:14][CH2:13][CH2:12][C:10]1[N:11]=[... | CS(=O)(=O)OCCCc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)c(F)n1 | CCS | 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 | 16 | A solution of ethanethiol in DMF was treated with sodium hydride, and then with 2-fluoro-4-(3-methanesulphonyloxypropyl)-1-triphenylmethylimidazole. After stirring at ambient temperature for 16 hours, the mixture was worked up by extraction and chromatography to give 4-(3-ethylthiopropyl)-2-fluoro-1-triphenylmethylimid... | CCSCCCc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)c(F)n1 | null | null | null |
454,933 | ord_dataset-4a5b4fffffb34daa876fff1f127a4135 | null | 2000-01-01T00:01:00 | true | Br[C@H:2]([CH2:10][OH:11])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[O:12]=[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15].CCCCCC.C(=O)([O-])[O-].[K+].[K+]>O>[O:11]1[CH2:10][C@@H:2]([C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[O:12][C:13]1([C:14]([O:16][CH2:17][CH3:18])=[O... | CCOC(=O)C(=O)C(=O)OCC | CC(C)(C)OC(=O)[C@H](Br)CO | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCCCCC | null | null | null | null | null | null | null | null | null | 25 | 15 | 6.90 g of tert-butyl (2R)-2-bromo-3-hydroxypropionate and 5.3 g of diethyl ketomalonate were mixed, and after the heat-generated reaction solution returned to room temperature, 15 ml of hexane and 6.4 g of potassium carbonate were sequentially added, followed by stirring at room temperature for 15 hours. Water was adde... | CCOC(=O)C1(C(=O)OCC)OC[C@@H](C(=O)OC(C)(C)C)O1 | null | 83 | null |
506,904 | ord_dataset-631d58dab387485c8eb0db4c20a232b7 | null | 2001-01-01T00:06:00 | true | [CH3:1][N:2]1[CH:6]=[C:5]([C:7]([O:9]CC)=[O:8])[CH:4]=[N:3]1.[OH-].[Na+]>C(O)C>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([OH:9])=[O:8])[CH:4]=[N:3]1 | CCOC(=O)c1cnn(C)c1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | 18 | A solution of ethyl 1-methyl-1H-pyrazole-4-carboxylate (20.2 g, 131 mmol) and NaOH (6.3 g, 158 mmol) in 200 mL absolute ethanol was refluxed for 2 h and stirring was continued at RT for 18 h. After that, the solvent was removed in vacuo. The residue was dissolved in water. The aq solution was washed with ether and acid... | Cn1cc(C(=O)O)cn1 | null | 86 | null |
528,394 | ord_dataset-f027aa93238e424fbbf9bad1c7699adc | null | 2001-01-01T00:12:00 | true | [NH2:1][C:2]1[N:10]=[C:9](Cl)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[Na+]>C(O)CCC>[NH2:1][C:2]1[N:10]=[C:9]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12... | Nc1nc(Cl)nc2c1ncn2Cc1ccccc1 | Nc1ccccc1 | null | [Na+] | [OH-] | 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 | 6-Amino-9-benzyl-2-chloropurine (100 mg, 0.385 mmol) and aniline (359 mg, 3.85 mmol) in 1-butanol (10 ml) were refluxed on heating for 20 hours. The reaction mixture was condensed in vacuo. To the residue was added 5N aqueous sodium hydroxide and the mixture was extracted with chloroform. The organic layer was dried on... | Nc1nc(Nc2ccccc2)nc2c1ncn2Cc1ccccc1 | null | 88.7 | null |
1,618,488 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [Cl:1][C:2]([F:14])([F:13])[C:3]1[NH:8][C:7](=[O:9])[C:6]([C:10]([OH:12])=O)=[CH:5][CH:4]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:27][O:28][CH2:29][CH2:30][NH2:31]>O1CCCC1>[Cl:1][C:2]([F:14])([F:13])[C:3]1[NH:8][C:7](=[O:9])[C:6]([C:10]([NH:31][CH2:30][CH2:29][O:28][CH3:27])=[O:12])=[CH:5][CH:4]=1 | COCCN | O=C(O)c1ccc(C(F)(F)Cl)[nH]c1=O | null | O=C(n1ccnc1)n1ccnc1 | 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 | 500 mg (2.2 mmol) of 6-[chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridine-3-carboxylic acid were dissolved in 10 ml of tetrahydrofuran, 508 mg (3.1 mmol) of N,N-carbonyldiimidazole were added and the mixture was then stirred initially at room temperature for 30 min and then under reflux for min. A solution of 202 mg (2... | COCCNC(=O)c1ccc(C(F)(F)Cl)[nH]c1=O | null | null | null |
130,335 | ord_dataset-2f37329a4b254471a74f2eb0981f11ec | null | 1985-01-01T00:05:00 | true | [Br:1][C:2]1[C:11]2[NH:10][C:9](=[O:12])[O:8][C:7]([CH3:14])([CH3:13])[C:6]=2[CH:5]=[C:4]([OH:15])[CH:3]=1.[C:16]1([S:22]([CH2:24][CH2:25][CH2:26][CH2:27]Br)=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[Br:1][C:2]1[C:11]2[NH:10][C:9](=[O:12])[O:8][C:7]([CH3:13])([CH3:14])[C:6]=2[CH:5]=[C:4]([O:15][CH2:27][CH2:26][C... | CC1(C)OC(=O)Nc2c(Br)cc(O)cc21 | O=S(CCCCBr)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 analogously to Example 4 from 8-bromo-6-hydroxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one and 4-phenylsulfinyl-butylbromide. | CC1(C)OC(=O)Nc2c(Br)cc(OCCCCS(=O)c3ccccc3)cc21 | null | null | null |
1,214,783 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | Cl.C(OC([N:9]1[C@H:14]([CH2:15][NH:16][C:17]2[N:22]=[CH:21][C:20]([Br:23])=[CH:19][N:18]=2)[CH2:13][C@H:12]2[C@@H:10]1[CH2:11]2)=O)(C)(C)C>O1CCOCC1>[C@H:10]12[CH2:11][C@H:12]1[CH2:13][C@@H:14]([CH2:15][NH:16][C:17]1[N:22]=[CH:21][C:20]([Br:23])=[CH:19][N:18]=1)[NH:9]2 | CC(C)(C)OC(=O)N1[C@H](CNc2ncc(Br)cn2)C[C@@H]2C[C@@H]21 | 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 HCl in dioxane (4.0 M, 30 mL) is added to a solution of (1S,3S,5S)-3-[(5-bromo-pyrimidin-2-ylamino)-methyl]-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (5.40 mmol) in dioxane (30 mL). After 2 h the solvents are removed in vacuo to give a crude product which is used without further purifi... | Brc1cnc(NC[C@@H]2C[C@@H]3C[C@@H]3N2)nc1 | null | null | null |
1,711,108 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [CH2:1]([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15][C@H:16]2[C:24]3[C:19](=[C:20]([O:26][C:27]4[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=4)[CH:21]=[CH:22][C:23]=3[F:25])[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)=[O:5])[CH3:2].[OH:34][C:35]([CH3:50])([CH3:49])[CH2:36][CH2:37]OS(C1C=CC(C)=CC=1)(=O... | CCOC(=O)[C@H]1C[C@@H]1c1ccc(O[C@@H]2CCc3c(Oc4ccc(O)cc4)ccc(F)c32)cc1 | Cc1ccc(S(=O)(=O)OCCC(C)(C)O)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 | null | 8 | (1S,2S)-2-{4-[(R)-7-Fluoro-4-(4-hydroxy-phenoxy)-indan-1-yloxy]-phenyl}-cyclopropanecarboxylic acid ethyl ester (Intermediate 7, 47 mg, 0.10 mmol), toluene-4-sulfonic acid 3-hydroxy-3-methyl-butyl ester (Intermediate 10, 54 mg, 0.21 mmol), and cesium carbonate (107 mg, 0.21 mmol) are suspended in dry N,N-dimethylformam... | CCOC(=O)[C@H]1C[C@@H]1c1ccc(O[C@@H]2CCc3c(Oc4ccc(OCCC(C)(C)O)cc4)ccc(F)c32)cc1 | null | null | null |
634,586 | ord_dataset-de283386b8034acd99fba96d3c7d3227 | null | 2004-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][C:19](=[O:21])[N:18]([NH:22][CH:23]3[CH2:28][CH2:27][N:26]([C:29]4[CH:34]=[CH:33][N:32]=[C:31]([CH3:35])[CH:30]=4)[CH2:25][CH2:24]3)[CH:17]([CH2:36][C:37]([O:39]C)=O)[CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.[NH3:41].C(O)C>>[Cl:1][C:2]... | N | COC(=O)CC1CN(S(=O)(=O)c2ccc3cc(Cl)ccc3c2)CC(=O)N1NC1CCN(c2ccnc(C)c2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | Methyl 4-[(6-chloro-2-naphthyl)sulfonyl]-1-[[1-(2-methyl-4-pyridinyl)-4-piperidinyl]amino]-6-oxo-2-piperazineacetate (100 mg) obtained in Example 138 and a 13% ammonia/ethanol solution (6.0 ml) were heated in a sealed tube at 90° C. for 6 hours. The reaction mixture was cooled and concentrated under reduced pressure. T... | Cc1cc(N2CCC(NN3C(=O)CN(S(=O)(=O)c4ccc5cc(Cl)ccc5c4)CC3CC(N)=O)CC2)ccn1 | null | null | null |
1,161,205 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [Cl:1][CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:34])([CH3:33])[C@@H:11]([O:23]CC1C=CC(OC)=CC=1)[C:12]([O:14][CH2:15][CH2:16][O:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:13])(=[O:7])=[O:6].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClCCl.O>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:33])([CH3:34])[C@@H:11... | CCOC(=O)OCCOC(=O)[C@H](OCc1ccc(OC)cc1)C(C)(C)COS(=O)(=O)CCCCl | null | null | N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | ClCCl | null | null | null | null | null | null | null | null | null | null | null | Following the general procedure for the oxidative cleavage of (4-methoxy)benzyl ethers of Description 19, (ethoxycarbonyloxy)ethyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-2-[(4-methoxyphenyl)methoxy]-3,3-dimethylbutanoate (36a) (0.77 g max.) dissolved in a mixture of dichloromethane (DCM) and water (10:1) (10 mL) was trea... | CCOC(=O)OCCOC(=O)[C@H](O)C(C)(C)COS(=O)(=O)CCCCl | null | 19 | null |
1,271,061 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:10][C:11]([C:16](=O)/[CH:17]=[CH:18]/N(C)C)=[CH:12][C:13]=1[C:14]#[N:15].C(=O)(O)O.[NH2:27][C:28]([NH2:30])=[NH:29].O>CN(C)C=O>[NH2:29][C:28]1[N:30]=[C:16]([C:11]2[NH:10][C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])=[C:13]([C:14]#[N:15])[CH:12]... | CN(C)/C=C/C(=O)c1cc(C#N)c(-c2ccc(Cl)cc2Cl)[nH]1 | N=C(N)N | null | O=C(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 110 | 22 | To a suspension of 2-(2,4-dichloro-phenyl)-5-((E)-3-dimethylamino-acryloyl)-1H-pyrrole-3-carbonitrile (6.80 g, 20.35 mmol) in 82 mL of N,N-dimethylformamide was added guanidine carbonate (9.17 g, 101.75 mmol). The mixture was heated to 110° C. for 18 hours under efficient stirring. Then, a further amount of guanidine c... | N#Cc1cc(-c2ccnc(N)n2)[nH]c1-c1ccc(Cl)cc1Cl | null | 83 | null |
699,821 | ord_dataset-bbd7e53f000345838ad4920a07a169ff | null | 2006-01-01T00:03:00 | true | [F:1][C:2]([F:16])([F:15])[C:3]1[CH:14]=[CH:13][C:6]([CH2:7][CH:8]([C:11]#[N:12])[C:9]#[N:10])=[CH:5][CH:4]=1.[H-].[Na+].I[CH2:20][CH2:21][C:22]([F:28])([F:27])[C:23]([F:26])([F:25])[F:24]>CN(C)C=O>[F:27][C:22]([F:28])([C:23]([F:26])([F:25])[F:24])[CH2:21][CH2:20][C:8]([CH2:7][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:15])([F:1... | N#CC(C#N)Cc1ccc(C(F)(F)F)cc1 | FC(F)(F)C(F)(F)CCI | 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 | null | null | Using 0.30 g of (4-(trifluoromethyl)benzyl)malononitrile, 6 ml of N,N-dimethylformamide, 0.60 g of sodium hydride (60% in oil), and 0.38 g of 4-iodo-1,1,1,2,2-pentafluorobutane, and according to the process described in the Production Example 1, there was obtained 0.30 g of 2-(3,3,4,4,4-pentafluorobutyl)-2-(4-(trifluor... | N#CC(C#N)(CCC(F)(F)C(F)(F)F)Cc1ccc(C(F)(F)F)cc1 | null | 60.6 | null |
616,024 | ord_dataset-31fc6d0085ca4d8dbbcd3a5fa9dcedfb | null | 2003-01-01T00:11:00 | true | [F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH2:12][C@H:11]([CH3:13])[NH:10][CH2:9][C@H:8]2[CH3:14])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:24][CH2:25][C:26](Cl)=[O:27]>ClCCl>[Cl:24][CH2:25][C:26]([N:10]1[CH2:9][C@H:8]([CH3:14])[N:7]([CH2:6][C:5]2[CH:15]=[CH:16][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:12][C@H:11]1[CH3:13])=[O:27] | O=C(Cl)CCl | C[C@@H]1CN[C@@H](C)CN1Cc1ccc(F)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 0.5 | To a solution of (2R, 5S)-1-(4-fluoro-benzyl)-2,5-dimethyl-piperazine (2.5 g, 11.25 mmol) in dry dichloromethane (11 ml) at 0° C. was added triethylamine (1.57 ml, 11.2 mmol) followed by chloroacetyl chloride (0.858 ml, 11.2 mmol). The resulting reaction mixture was stirred for 30 minutes. The reaction was then filtere... | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)CCl | null | 84.9 | null |
1,680,894 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][C:11]([NH:13][C:14]2[N:19]=[CH:18][C:17]3[C:20]([NH:42][CH3:43])=[N:21][N:22](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:16]=3[CH:15]=2)=[O:12])[CH3:9])=[CH:4][CH:3]=1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][C:11]([NH:13][C:14]2[N:19]=[... | CNc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)c2cc(NC(=O)N[C@H](C)c3ccc(F)cc3)ncc12 | null | null | CC[SiH](CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | (R)-1-(1-(4-Fluorophenyl)ethyl)-3-(3-(methylamino)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)urea (404 mg, 0.708 mmol) and triethylsilane (0.170 mL, 1.062 mmol) were stirred in TFA (5 mL) at room temperature for 30 min. The solvent was removed in vacuo, saturated NaHCO3 was added, and the products extracted into EtOAc (×... | CNc1n[nH]c2cc(NC(=O)N[C@H](C)c3ccc(F)cc3)ncc12 | null | null | null |
1,022,628 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=3)[C:14]#[N:15])[N:10]=2)[N:7]=1.CO.[CH3:21][NH2:22]>>[CH3:21][NH:22][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=3)[C:14]#[N:15])[N:10]=2)[N:7]=1 | CN | N#Cc1cccc(-c2cn3nc(Cl)ccc3n2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 125 | null | A mixture of 3-(6-chloroimidazo[1,2-b]pyridazin-2-yl)benzonitrile (0.25 mmol) and 10 mL methylamine methanol solution was heated at 125° C. in microwave synthesizer for 30 min. After purification to provide 3-(6-(methylamino)imidazo[1,2-b]pyridazin-2-yl)benzonitrile. | CNc1ccc2nc(-c3cccc(C#N)c3)cn2n1 | null | null | null |
1,449,674 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[N:45]12[CH2:52][CH2:51][CH:48]([CH2:49][CH2:50]1)[C@@H:47](O)[CH2:46]2>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:1... | O[C@H]1CN2CCC1CC2 | CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)O | null | C(=NC1CCCCC1)=NC1CCCCC1 | On1nnc2ccccc21 | 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 | A mixture of (S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid (500 mg, 1.88 mmol), DCC (467 mg, 2.26 mmol), and HOBT (346 mg, 2.26 mmol) in dry THF (15 ml) was stirred for 30 minutes at RT. Then (R)-quinuclidin-3-ol (288 mg, 2.26 mmol) was added portionwise and the reaction was stirred at RT for 16 hours. The so... | CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)O[C@H]1CN2CCC1CC2 | null | 85.2 | null |
763,570 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | [NH2:1][CH2:2][C:3]([C:6]1[NH:7][C:8]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[C:16](=[O:20])[CH2:15][CH2:14]3)[N:10]=1)([CH3:5])[CH3:4].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.Cl.[CH3:53][O:54][CH2:55][CH2:56][N:57]1[CH2:62][CH2:61][CH:60]([C:63](O)=[O:64]... | COCCN1CCC(C(=O)O)CC1 | CC(C)(CN)c1nc(-c2ccc3c(c2)CCC3=O)c(-c2ccncc2)[nH]1 | null | C(=NC1CCCCC1)=NC1CCCCC1 | Cl | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 0.5 | A mixture of the product of Example 1, Step 6 (0.1 g, 0.29 mmol), 1-hydroxybenzotriazole (0.06 g, 0.44 mmol) and polymer bound 1,3-dicyclohexylcarbodiimide (0.4 g, 0.6 mmol, 1.52 mmol/g) in a 1:1 mixture of dichloromethane and DMF (4 ml) was stirred at room temperature for 30 min. A solution of 1-(2-methoxy-ethyl)-pipe... | COCCN1CCC(C(=O)NCC(C)(C)c2nc(-c3ccncc3)c(-c3ccc4c(c3)CCC4=O)[nH]2)CC1 | null | 80.2 | null |
1,239,403 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [CH2:1]([NH:3][CH2:4][C:5]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:6]=1[OH:15])[CH3:2].C(NC(C)C)(C)C.Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>C(Cl)Cl>[CH2:27]([O:26][C:24](=[O:25])[N:3]([CH2:1][CH3:2])[CH2:4][C:5]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12]... | CCNCc1cc(S(C)(=O)=O)ccc1O | O=C(Cl)OCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CC(C)NC(C)C | null | null | null | null | null | null | null | null | null | null | null | To 2-ethylaminomethyl-4-methanesulfonyl-phenol (0.229 g, 1.0 mmol) and diisopropylamine (0.94 mL, 2.5 mmol) in CH2Cl2 (10 mL) was added benzyl chloroformate (0.16 mL, 1.1 mmol). Some over-acylation product was observed, so additional benzyl chloroformate (0.21 mL) was added to convert all of the product to the diacylat... | CCN(Cc1cc(S(C)(=O)=O)ccc1O)C(=O)OCc1ccccc1 | null | null | null |
114,948 | ord_dataset-d182ca8cf3f34de69c7a38343db8c930 | null | 1984-01-01T00:03:00 | true | [C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].[NH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[C:1]([CH2:3][C:4]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:6])#[N:2] | N#CCC(=O)O | NCc1ccccn1 | null | C(=NC1CCCCC1)=NC1CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | 5 | To a solution of 6.8 g of cyanoacetic acid in 200 ml of acetonitrile was added a solution of 8.65 g of 2-aminomethylpyridine in 50 ml of acetonitrile, and to the resulting suspension there was added rapidly (with stirring) a solution of 18.5 g of dicyclohexylcarbodiimide in 50 ml of acetonitrile. After stirring 5 hours... | N#CCC(=O)NCc1ccccn1 | null | null | null |
1,610,995 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [Cl:1][C:2]1[C:3]([F:35])=[C:4]([CH:32]=[CH:33][CH:34]=1)[CH2:5][NH:6][C:7]([C@@H:9]1[CH2:14][C@@H:13]2[C@@H:11]([CH2:12]2)[N:10]1[C:15](=[O:31])[CH2:16][N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:26]#[N:27])[CH:24]=2)[C:19]([C:28](=[O:30])[CH3:29])=[CH:18]1)=[O:8].[N-:36]=[N+:37]=[N-:38].[Na+]>O.C(O)(C)C.[Br-].[Zn+... | [N-]=[N+]=[N-] | CC(=O)c1cn(CC(=O)N2[C@@H]3C[C@@H]3C[C@H]2C(=O)NCc2cccc(Cl)c2F)c2cc(C#N)ccc12 | null | [Br-] | [Na+] | [Zn+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(C)O | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in a similar manner as described above for Example 617 from (1R,3S,5R)-2-[2-(3-acetyl-6-cyano-indol-1-yl)-acetyl]-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid 3-chloro-2-fluoro-benzylamide (prepared as described in Example 616 (100.0 mg, 0.203 mmol), sodium azide (66.0 mg, 1.014 mmol) an... | CC(=O)c1cn(CC(=O)N2[C@@H]3C[C@@H]3C[C@H]2C(=O)NCc2cccc(Cl)c2F)c2cc(-c3nnn[nH]3)ccc12 | null | null | null |
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