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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,754,318 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [OH:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][C:9]([OH:11])=O)[O:4][N:3]=1.CCN(C(C)C)C(C)C.[C:21]([N:28]1[CH2:33][CH2:32][CH:31]([CH2:34][NH2:35])[CH2:30][CH2:29]1)([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CN(C=O)C>[OH:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][C:9]([NH:35][CH2:34][CH:31]2[CH2:32][CH2:33][N:28]([C:21]([O:23... | CC(C)(C)OC(=O)N1CCC(CN)CC1 | O=C(O)CCc1cc(O)no1 | null | null | null | 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 | 0.08 | To 3-(3-hydroxyisoxazol-5-yl)propanoic acid (300 mg, 1.909 mmol) in DMF (7 mL) was added DIPEA (0.667 mL, 3.82 mmol) followed by 1-[(1-(cyano-2-ethoxy-2-oxoethylideneaminooxy)dimethylaminomorpholino)]uronium hexafluorophosphate (COMU) (981 mg, 2.291 mmol). The resulting brown solution was stirred at RT for 5 mins and t... | CC(C)(C)OC(=O)N1CCC(CNC(=O)CCc2cc(O)no2)CC1 | null | null | null |
1,751,943 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [CH:1]1([CH2:4][N:5]2[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[N:6]2)[CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([CH2:4][N:5]2[CH:9]=[C:8]([NH2:10])[CH:7]=[N:6]2)[CH2:3][CH2:2]1 | O=[N+]([O-])c1cnn(CC2CC2)c1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of 1-(cyclopropylmethyl)-4-nitro-1H-pyrazole (8.37 g, 50.1 mmol) in methanol (150 mL) was added 10% Pd/C (840.0 mg, 0.7893 mmol). The suspension was stirred at room temperature under a H2 atmosphere for 2 h. Filtered and the filter cake was washed with MeOH (50 mL×3). The filtrate was concentrated in vacu... | Nc1cnn(CC2CC2)c1 | null | 80 | null |
382,178 | ord_dataset-f367d8d2baac490b9204609a79420961 | null | 1997-01-01T00:11:00 | true | [OH-].[Na+].[CH3:3][O:4][C:5]1[CH:30]=[CH:29][C:8]([CH2:9][N:10]2[C:14]([C:15]([O-:17])=[O:16])=[C:13]([C:18](=[O:28])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N+:25]([O-:27])=[O:26])[N:12]=[N:11]2)=[CH:7][CH:6]=1.Cl>O1CCCC1>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]2[C:14]([C:15]([OH:17])=[O:16])=[C:13]([C... | COc1ccc(Cn2nnc(C(=O)c3ccccc3[N+](=O)[O-])c2C(=O)[O-])cc1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 2 | A 1N aqueous sodium hydroxide solution (50 ml) was added to a solution of 1-(4-methoxybenzyl)-4-(2-nitrobenzoyl)-1,2,3-triazole-5-carboxylate (b-1) (10.17 g, 24.8 mmole) in tetrahydrofuran (100 ml), which was stirred at room temperature for 2 hours. The aqueous layer was acidified with hydrochloric acid, extracted with... | COc1ccc(Cn2nnc(C(=O)c3ccccc3[N+](=O)[O-])c2C(=O)O)cc1 | null | null | null |
1,041,676 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [C:1]([O:5][C:6](=[O:32])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:30])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[CH:24]=3)=[CH:17][C:16]=2[NH2:31])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C([C:35]1[C:36]([N:42]=[CH:43][N:44]([CH3:46])C)=[N:37][C:38]([CH3:41])=[CH:39][C... | CC(C)(C)OC(=O)Nc1ccc(Sc2ccc(C(=O)Nc3cccc(Br)c3)cc2N)cc1 | Cc1ccc(C#N)c(N=CN(C)C)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The product of Example 64A was reacted with the product of Example 9B using the procedure of Example 13D substituting the product of Example 64A for the product of Example 13C and substituting the product of Example 9B for the product of Example 8E to provide the crude title compound which was purified by column chroma... | Cc1ccc2c(Nc3cc(C(=O)Nc4cccc(Br)c4)ccc3Sc3ccc(NC(=O)OC(C)(C)C)cc3)ncnc2n1 | null | 21 | null |
117,849 | ord_dataset-3708161f4ba04e959b9a7a8d59fd86e1 | null | 1984-01-01T00:05:00 | true | [CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[CH2:15][CH:14]([N:19]=[N+]=[N-])[CH2:13][CH2:12][C:11]=2[C:10]=1[C:22]([NH2:24])=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C)C.[BH4-].[Na+].Cl>O>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[CH2:15][CH:14]([NH2:19])[CH2:13][CH2:12][C:11]=2[C:10]=1[C:22]([NH2:24])=[O:23])... | [N-]=[N+]=NC1CCc2c(ccc(OCc3ccccc3)c2C(N)=O)C1 | null | null | Cl | [BH4-] | [Na+] | 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 | null | A solution was prepared from 3.4 g. of dl-2-benzyloxy-6-azido-5,6,7,8-tetrahydro-1-naphthalenecarboxamide (from Example 4) and 100 ml. of isopropanol. The solution was cooled and 0.5 g. sodium borohydride added thereto in small portions. After the addition had been completed, the reaction mixture was heated to reflux t... | NC(=O)c1c(OCc2ccccc2)ccc2c1CCC(N)C2 | null | null | null |
1,745,103 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[Cl:12])[CH:5]=[C:4]([C@@H:13]([NH:15][C:16]2[N:24]=[CH:23][N:22]=[C:21]3[C:17]=2[N:18]=[CH:19][N:20]3[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[CH3:14])[N:3]=1.O.[CH3:35][N:36](C=O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([... | CN(C)C=O | COc1ccc(Cn2cnc3c(N[C@@H](C)c4cc5cccc(Cl)c5c(Cl)n4)ncnc32)cc1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 100 | 8 | To a stirred solution of ((S)—N-(1-(1,8-dichloroisoquinolin-3-yl)ethyl)-9-(4-methoxybenzyl)-9H-purin-6-amine 1 (1.5 g, 3.1 mmol, 1.0 eq) and tetrakis(triphenylphosphine)palladium (181 mg, 0.16 mmol, 0.05 eq) in DMF (50 mL) at RT, dicyanozine (476 mg, 4.06 mmol, 1.3 eq) was added and the resulting mixture was stirred at... | COc1ccc(Cn2cnc3c(N[C@@H](C)c4cc5cccc(Cl)c5c(C#N)n4)ncnc32)cc1 | null | null | null |
852,804 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | [C:1]([C:3]1[CH:15]=[CH:14][C:6]2[O:7][CH2:8][C:9]([CH3:13])([CH3:12])[CH2:10][O:11][C:5]=2[CH:4]=1)#[CH:2].I[C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][CH:18]=1>>[CH3:13][C:9]1([CH3:12])[CH2:8][O:7][C:6]2[CH:14]=[CH:15][C:3]([C:1]#[C:2][C:17]3[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][CH:... | CC(=O)c1ccc(I)cc1 | C#Cc1ccc2c(c1)OCC(C)(C)CO2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound is prepared in analogy to example 1 from 7-ethynyl-3,3-dimethyl-3,4-dihydro-2H-benzo[b][1,4]dioxepine (6) (example 1d) and 1-(4-iodo-phenyl)-ethanone. MS (ESI) 320.2 (M•)+. | CC(=O)c1ccc(C#Cc2ccc3c(c2)OCC(C)(C)CO3)cc1 | null | null | null |
1,155,534 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [C:1]([CH:3]1[C:12]2[CH2:11][CH2:10][C:9]3=[N:13][N:14]([CH2:16][C:17]4[C:22]([CH3:23])=[C:21]([O:24][CH3:25])[C:20]([CH3:26])=[CH:19][N:18]=4)[N:15]=[C:7]([C:8]=23)[C:6]([N:27](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[N:5][S:4]1)#[N:2].Cl.C(N(CC)CC)C.[N-:50]=[N+:51]=[N-:52].[Na+]>CN(C)C=O>[CH3:25][O:24][C:21]1[C:20]([CH3:26])=... | COc1c(C)cnc(CN2N=C3CCC4=C3C(=N2)C(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=NSC4C#N)c1C | [N-]=[N+]=[N-] | null | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 105 | 15 | A mixture composed of di-tert-butyl {7-cyano-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7,8,9-tetrahydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}imidodicarbonate of Step 4) of Example 23 (53 mg), N,N-dimethylformamide (1 mL), triethylamine hydrochloride (14.5 m) and sodium azide (6.8 mg) was sealed in a tube ... | COc1c(C)cnc(CN2N=C3CCC4=C3C(=N2)C(N)=NSC4c2nnn[nH]2)c1C | null | 19 | null |
428,592 | ord_dataset-8cce6f317d644b348a7978a2dce3ea01 | null | 1999-01-01T00:03:00 | true | I[CH2:2][C:3]([O:5][CH:6]([C:9]1[CH:25]=[C:24]2[N:12]([CH2:13][C:14]3[C:15]2=[N:16][C:17]2[C:22]([CH:23]=3)=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11](=[O:26])[C:10]=1[CH3:27])[CH2:7][CH3:8])=[O:4].[NH:28]1[CH:32]=[CH:31][N:30]=[CH:29]1.[ClH:33]>O>[ClH:33].[N:28]1([CH2:2][C:3]([O:5][CH:6]([C:9]2[CH:25]=[C:24]3[N:12]([CH2:1... | CCC(OC(=O)CI)c1cc2n(c(=O)c1C)Cc1cc3ccccc3nc1-2 | c1c[nH]cn1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared according to the procedure in Example 13 except using (±)-7-[1-[(iodoacetyl)oxy]propyl]-8-methylindolizino[1,2-b]quinolin-9(11H)-one and imidazole. 1H NMR (CDCl3 /MeOH-d4) d 9.17 (s, 1H), 8.60 (s, 1H), 8.34 (d, 1H), 8.04 (d, 1H), 7.95 (m, 1H), 7.75 (m, 1H), 7.61 (s, 1H), 7.51 (br s, 1H),... | CCC(OC(=O)Cn1ccnc1)c1cc2n(c(=O)c1C)Cc1cc3ccccc3nc1-2 | null | null | null |
1,671,505 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[C:17]3[C:18]4[C@H:19]([CH2:29][C:30](OCC)=[O:31])[CH2:20][CH2:21][CH2:22][C:23]=4[S:24][C:25]=3[N:26]=[CH:27][N:28]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:31][CH2:30][CH2:29][C@H:19]1[C:18]2[C:... | CCOC(=O)C[C@@H]1CCCc2sc3ncnc(OC4CCC(NC(=O)OC(C)(C)C)CC4)c3c21 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of ethyl 2-[(13S)-3-[(4-[[(tert-butoxy)carbonyl]amino]cyclohexyl)oxy]-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-13-yl]acetate (800 mg, 1.63 mmol, 1.00 equiv) in THF (30 mL) in an ice/water bath under nitrogen was added LiAlH4 (121.2 mg, 3.20 mmol, 2.00 equiv). The resulting solut... | CC(C)(C)OC(=O)NC1CCC(Oc2ncnc3sc4c(c23)[C@H](CCO)CCC4)CC1 | null | 67.2 | null |
295,903 | ord_dataset-ec7cb3d5a8704f64b01d401ea555974f | null | 1994-01-01T00:09:00 | true | C[O:2][C:3](=[O:23])[C:4](=[O:22])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:7][CH:6]=1.[OH-].[Na+]>CO.O>[O:22]=[C:4]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:9][CH:10]=1)[C:3... | COC(=O)C(=O)c1ccc(OCCCCc2cccnc2)cc1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | null | null | A mixture of alpha-oxo-4-[4-(3-pyridinyl)butoxy]benzeneacetic acid methyl ester (4:1) molar hydrate (1.1 g) in hot methanol (10 mL) was treated with 1N sodium hydroxide (5 mL) and diluted with water. The organic solvent was removed under vacuum and the residue in water was washed with diethyl ether. The aqueous layer w... | O=C(O)C(=O)c1ccc(OCCCCc2cccnc2)cc1 | null | null | null |
1,480,759 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [C:1]1(=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]2([CH2:12][CH2:11]2)[C:3](=O)[NH:2]1.B.CO>C1COCC1>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]2([CH2:12][CH2:11]2)[CH2:3][NH:2]1 | O=C1NC(=O)C2(CC2)c2ccccc21 | null | null | B | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | 0 | null | 0.5 g (2.7 mmol) 1′H-spiro[cyclopropane-1,4′-isoquinoline]-1′,3′(2′H)-dione in 50 mL THF were heated to the reflux temperature of the solvent. 11 mL (11 mmol) of a 1M borane in THF solution were added dropwise and the mixture was refluxed for 3 h. The reaction mixture was cooled to 0° C. and mixed with 50 mL methanol. ... | c1ccc2c(c1)CNCC21CC1 | null | null | null |
127,767 | ord_dataset-e61c1950b2fc468dbf0701c65768f73f | null | 1985-01-01T00:03:00 | true | [C:1]1([S:7][C:8]2[CH2:14][CH:13]3[CH:10]([C:11](=[O:18])[CH:12]3[CH:15]([OH:17])[CH3:16])[C:9]=2[C:19]([O:21][CH:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:43])C=1>C(Cl)Cl>[C:1]1([S:7]([C:8]2[CH2:14][C... | O=C(OO)c1cccc(Cl)c1 | CC(O)C1C(=O)C2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(Sc3ccccc3)CC21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 0.75 | To a solution of 200 mg of 3-phenylthio-6-(1-hydroxyethyl)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid, diphenylmethyl ester, in 15 mL of methylene chloride at -50° under nitrogen was added 90 mg of m-chloroperbenzoic acid in 3 mL of methylene chloride. The solution was stirred at -40° for 45 min and then warmed to ... | CC(O)C1C(=O)C2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(S(=O)c3ccccc3)CC21 | null | 69.6 | null |
900,148 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [NH2:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1>O>[CH3:5][C:4]1[N:1]([C:2]2[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=2)[C:10]([CH3:9])=[CH:2][CH:3]=1 | N#CCc1ccc(N)cc1 | null | 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 | null | null | 20 g (0.15 mol) of p-aminobenzyl cyanide, 19 ml (0.17 mol) of 2,5-dicetohexane and 2.88 g (0.015 mol) of hydrated p-toluene sulphonic acid are dissolved in a 500 ml flask. This mixture is heated to reflux, the water formed is trapped using a Dean Stark apparatus. At the end of the reaction, the solvent is evaporated of... | Cc1ccc(C)n1-c1ccc(CC#N)cc1 | null | 34 | null |
237,027 | ord_dataset-56e7a343b17a4d6da818127ceb19589d | null | 1991-01-01T00:11:00 | true | ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[CH:15]([C:18]1[NH:19][C:20]([CH:41]([CH3:43])[CH3:42])=[C:21]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH:22]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C:23]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25])([CH3:17])[CH3:16]>C(Cl)Cl>[CH:41]([C:20]1[C:21]([C:36]([O:38][CH2:39][CH3:40]... | CCOC(=O)C1=C(C(C)C)NC(C(C)C)=C(C(=O)OCC)C1c1ccc(F)cc1 | 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 | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 1 | 3.8 g (16.4 mmol) of 2,3-dichloro-5,6-dicyano-p-benzoquinone are added to a solution of 6.6 g (16.4 mmol) of the compound from Example II in 200 ml of methylene chloride p.A. and the mixture is stirred at room temperature for 1 hour. It is then filtered through kieselguhr with suction, and the methylene chloride phase ... | CCOC(=O)c1c(C(C)C)nc(C(C)C)c(C(=O)OCC)c1-c1ccc(F)cc1 | null | null | null |
576,343 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | C1(CN2CCC(C[CH2:15][C:16]3[C:20]4[CH:21]=[CH:22][C:23]5[NH:27][C:26](=[O:28])[CH2:25][C:24]=5[C:19]=4[O:18][N:17]=3)CC2)C=CC=CC=1.N1C=CC=CC=1>CN(C=O)C>[CH3:15][C:16]1[C:20]2[CH:21]=[CH:22][C:23]3[NH:27][C:26](=[O:28])[CH2:25][C:24]=3[C:19]=2[O:18][N:17]=1 | O=C1Cc2c(ccc3c(CCC4CCN(Cc5ccccc5)CC4)noc23)N1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | The procedure described in Example 33d was followed with the oxime acetate obtained in step c (0.334 g, 1.35 mmol) and pyridine (0.55 mL, 6.75 mmol) in DMF (25 mL). After work-up, the residue was purified by silica gel flash chromatography (50→75% EtOAc-hexanes) to give the title compound (0.086 g, 34%) as a white soli... | Cc1noc2c3c(ccc12)NC(=O)C3 | null | 33.9 | null |
1,515,890 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:18]([F:21])([CH3:20])[CH3:19])=[N:7][N:8]2[C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=2)=[CH:4][CH:3]=1.[CH3:22][C:23]1[O:27][N:26]=[C:25]([C@:28]([OH:32])([C:30]#[CH:31])[CH3:29])[N:24]=1>N1CCCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2... | C#C[C@@](C)(O)c1noc(C)n1 | CC(C)(F)c1nn(-c2ccnc(N)n2)c2cc(Br)ccc12 | null | [Cu]I | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | 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 | 66 | null | To a solution of 4-[6-bromo-3-(2-fluoropropan-2-yl)-1H-indazol-1-yl]pyrimidin-2-amine (95 mg, 0.26 mmol) in piperidine (1 mL) was introduced tetrakis(triphenylphosphine)palladium (0) (24 mg, 0.02 mmol), copper(I) iodide (4 mg, 0.02 mmol) and (2R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)but-3-yn-2-ol (79 mg, 0.52 mmol). The re... | Cc1nc([C@](C)(O)C#Cc2ccc3c(C(C)(C)F)nn(-c4ccnc(N)n4)c3c2)no1 | null | null | null |
1,001,517 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | [H-].[Na+].C1COCC1.[N:8]1([CH2:14][CH2:15][CH2:16][OH:17])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[CH2:18]([C:20]1[N:21]=[N+:22]([O-:31])[C:23]2[CH:29]=[CH:28][C:27](F)=[CH:26][C:24]=2[N:25]=1)[CH3:19]>O>[CH2:18]([C:20]1[N:21]=[N+:22]([O-:31])[C:23]2[CH:29]=[CH:28][C:27]([O:17][CH2:16][CH2:15][CH2:14][N:8]3[CH2:13][CH2:... | CCc1nc2cc(F)ccc2[n+]([O-])n1 | OCCCN1CCOCC1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 20 | 0.33 | NaH (60% dispersion in oil, 310 mg, 7.75 mmol) was added to dry THF (10 mL) and stirred at 20° C. for 20 min prior to the addition of 3-(4-morpholinyl)propanol (676 mg, 4.66 mmol). The mixture was stirred for 30 min, fluoride 28 (300 mg, 1.55 mmol) added and the resulting solution stirred at 20° C. for 2.5 h under N2. ... | CCc1nc2cc(OCCCN3CCOCC3)ccc2[n+]([O-])n1 | null | 52.1 | null |
645,841 | ord_dataset-c975a50a7600448fabd558f4a94a3e29 | null | 2004-01-01T00:08:00 | true | [CH3:1][C:2]1[CH:13]=[C:12]2[C:5]([NH:6][CH:7]=[C:8]2[CH2:9][CH2:10][NH2:11])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[N+:19]([C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:23]=1F)([O-:21])=[O:20]>O.C(O)C>[N+:19]([C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:23]=1[NH:11][CH2:10][CH2:9][C:8]... | Cc1ccc2[nH]cc(CCN)c2c1 | O=[N+]([O-])c1ccc(F)c([N+](=O)[O-])c1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | 25 | 2 | 1 mMole of 5-metyltryptamine was dissolved in 100 ml of water and the pH was adjusted to pH 8.3 with 2.5 moles of sodium bicarbonate (NaHCO3), A 1.5% solution of 2,4-dinitrofluorobenzene in 200 ml ethanol was added and the mixture was stirred during 2 hours at room temperature. The desired product precipitates out, it ... | Cc1ccc2[nH]cc(CCNc3ccc([N+](=O)[O-])cc3[N+](=O)[O-])c2c1 | null | 85 | null |
285,405 | ord_dataset-d63ab258f4634f87bdebbaff0a341c28 | null | 1994-01-01T00:02:00 | true | [C:1]1([C:7]2[NH:8][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]1([C:16](=[O:22])[CH2:17][C:18](=O)[CH2:19][CH3:20])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C>[CH2:19]([C:18]1[NH:8][CH:9]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:17]=1[C:16](=[O:22])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:20... | C1=C(c2ccccc2)N1 | CCC(=O)CC(=O)c1ccccc1 | 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 | 8 | The preparation is carried out in accordance with the general procedure in Example 1. The reactants are 2-phenylazirine and 1-phenylpentane-1,3-dione. The reaction product is dissolved in 150 ml of hot ethanol and the solution is allowed to stand overnight at room temperature. The precipitated crystals are filtered wit... | CCc1[nH]cc(-c2ccccc2)c1C(=O)c1ccccc1 | null | null | null |
1,708,018 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([I:16])=[CH:9][CH:10]=3)[C@@:5]3([N:21]=[C:20]([NH:22]C(=O)OC(C)(C)C)[CH2:19][O:18][CH2:17]3)[C:4]=2[CH:3]=1.FC(F)(F)C(O)=O>>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([I:16])=[CH:9][CH:10]=3)[C@@:5]3([N:21]=[C:20]([NH2:22])[CH2:19... | CC(C)(C)OC(=O)NC1=N[C@@]2(COC1)c1cc(Br)ccc1Oc1ccc(I)cc12 | 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 | null | null | null | null | null | null | null | null | null | null | null | 2 | In a 150-mL resealable vessel, the (S)-tert-butyl 2′-bromo-7′-iodo-2,6-dihydrospiro[[1,4]oxazine-3,9′-xanthene]-5-ylcarbamate (1.475 g, 2.58 mmol) was dissolved in dcm (10 mL), and 2,2,2-trifluoroacetic acid (1.989 mL, 25.8 mmol) was added. The vessel was sealed and placed in a 50° C. oil bath. After 2 h, the reaction ... | NC1=N[C@@]2(COC1)c1cc(Br)ccc1Oc1ccc(I)cc12 | null | 12.4 | null |
1,264,726 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [OH:1][C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)([CH3:7])[C:3]([O:5]C)=O.F[C:19]1[C:28]([N+:29]([O-])=O)=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]([C:32](F)(F)F)[CH:20]=1>>[CH3:7][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:3](=[O:5]... | COC(=O)C(C)(O)c1cccc(C(F)(F)F)c1 | COC(=O)c1cc([N+](=O)[O-])c(F)cc1C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using methyl 2-hydroxy-2-[3-(trifluoromethyl)phenyl]propanoate and methyl 4-fluoro-5-nitro-2-(trifluoromethyl)benzoate, the title compound was obtained in a similar manner to Reference Example 22 and Reference Example 2. | COC(=O)c1cc2c(cc1C)OC(C)(c1cccc(C(F)(F)F)c1)C(=O)N2 | null | null | null |
1,330,932 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [S:1]([Cl:5])(Cl)(=[O:3])=[O:2].[CH3:6][C@H:7]1[O:12][C@@H:11]([CH3:13])[CH2:10][NH:9][CH2:8]1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:13][C@H:11]1[O:12][C@@H:7]([CH3:6])[CH2:8][N:9]([S:1]([Cl:5])(=[O:3])=[O:2])[CH2:10]1 | O=S(=O)(Cl)Cl | C[C@@H]1CNC[C@H](C)O1 | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 24 | Sulfuryl dichloride (0.363 ml, 4.47 mmol) was added at room temperature to a solution of cis-2,6-dimethylmorpholine (0.500 ml, 4.06 mmol) and 4-dimethylaminopyridine (496 mg, 4.06 mmol) in CH2Cl2 (5 ml) and the whole was stirred at room temperature for 24 hours. The reaction mixture was quenched with H2O (10 ml) and ex... | C[C@@H]1CN(S(=O)(=O)Cl)C[C@H](C)O1 | null | null | null |
413,620 | ord_dataset-275344fd078b4340b89ca0b6e92beb95 | null | 1998-01-01T00:10:00 | true | [C:1]1([CH3:15])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1OS(C(F)(F)F)(=O)=O.[CH2:16]([NH2:20])[CH2:17][CH2:18][CH3:19]>>[CH2:16]([NH:20][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:15])[CH2:17][CH2:18][CH3:19] | Cc1ccccc1OS(=O)(=O)C(F)(F)F | CCCCN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | General procedure B using 55.1 mg (0.229 mmol) of o-tolyltriflate and 34.0 μl (0.344 mmol) of n-butylamine gave 67% yield of N-butyl-2-methylaniline after silica gel chromatograph using 5% ethyl acetate in hexanes. | CCCCNc1ccccc1C | null | 67 | null |
210,520 | ord_dataset-e0a818f9350b46cdb184d2ac404ede9f | null | 1990-01-01T00:06:00 | true | [N:1]1([C:7]2[S:8][CH:9]=[C:10]([C:12](OCC)=[O:13])[N:11]=2)[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[N:1]1([C:7]2[S:8][CH:9]=[C:10]([CH2:12][OH:13])[N:11]=2)[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1 | CCOC(=O)c1csc(N2CCSCC2)n1 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | The reaction described in Preparation 15 was repeated, but using 1.5 g of ethyl 2-(thiomorpholin-4-yl)thiazole -4-carboxylate, 0.26 g of lithium aluminum hydride and 15 ml of tetrahydrofuran, giving the title compound as a colorless powder. | OCc1csc(N2CCSCC2)n1 | null | null | null |
726,870 | ord_dataset-eb4226b4f7644a01a737e7547b70014a | null | 2006-01-01T00:09:00 | true | [CH2:1]([N:8]1[CH2:13][CH:12]2[CH2:14][CH:9]1[CH2:10][N:11]2[CH2:15][C:16]#[N:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Ni].N>[CH2:1]([N:8]1[CH2:13][CH:12]2[CH2:14][CH:9]1[CH2:10][N:11]2[CH2:15][CH2:16][NH2:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | N#CCN1CC2CC1CN2Cc1ccccc1 | null | null | [Ni] | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 5.74 g (25.3 mmoles) of 140 and 50 mL of NH3 were hydrogenated with 2 g of Raney nickel in a steel autoclave at 100 bar H2 and 100° C. for 2 hours. The catalyst was filtered off with suction and the solution was evaporated and distilled using a bulb tube (boiling point: 135°–145° C. at 0.01 mbar): 5.02 g ... | NCCN1CC2CC1CN2Cc1ccccc1 | null | 85.8 | null |
315,037 | ord_dataset-bd998d3fe946475e835418aaf647c00d | null | 1995-01-01T00:08:00 | true | Cl[C:2](Cl)([C:12]([CH3:14])=[O:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[H][H]>O.C1(C)C=CC=CC=1.[H][H]>[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:4])[CH2:2][C:12]([CH3:14])=[O:13] | [H][H] | CC(=O)C(Cl)(Cl)C(=O)Nc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | O | null | null | null | null | null | null | null | null | null | null | null | 2.46 g (0.01 mole) of α,α-dichloroacetoacetanilide was dissolved in 20 ml of water and 30 ml of toluene, and dehalogenated with hydrogen using 5% Pd/C as catalyst. Hydrogen was allowed to react until no more would be absorbed. The first equivalent (251 ml at 739 mm pressure and 25° C.) was absorbed in 50 minutes (a rat... | CC(=O)CC(=O)Nc1ccccc1 | null | null | null |
1,442,867 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [Cl:1][C:2]1[S:14][C:5]2=[N:6][C:7]([Cl:13])=[C:8]([C:10](=[O:12])[CH3:11])[CH:9]=[C:4]2[CH:3]=1>C1COCC1>[Cl:1][C:2]1[S:14][C:5]2=[N:6][C:7]([Cl:13])=[C:8]([C@H:10]([OH:12])[CH3:11])[CH:9]=[C:4]2[CH:3]=1 | CC(=O)c1cc2cc(Cl)sc2nc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 1 | 1-(2,6-Dichlorothieno[2,3-b]pyridin-5-yl)ethanone (3.6 g, 14.63 mmol) was dissolved in THF (100 mL) and ccoled to −55° C. in a dry ice/MeCN bath. To this solution was added a solution of (+)-dip-chloride(tm) (10.32 g, 32.2 mmol) in THF dropwise. The reaction was allowed to warm slowly to rt overnight and quenched by ad... | C[C@@H](O)c1cc2cc(Cl)sc2nc1Cl | null | null | null |
1,036,309 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@@H:18]([C:29](O)=[O:30])[CH2:19][C:20]3[CH:25]=[C:24]([CH3:26])[C:23]([OH:27])=[C:22]([CH3:28])[CH:21]=3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:32]=[CH:33][CH:34]=[CH:35][C:4]=2[NH:3]1.[CH3:36][N:37]1[CH2:42][CH2:41][CH:40]([CH:43]2[CH2:48][CH2:... | CN1CCC(C2CCNCC2)CC1 | Cc1cc(C[C@@H](OC(=O)N2CCC(N3CCc4ccccc4NC3=O)CC2)C(=O)O)cc(C)c1O | null | null | null | null | null | null | null | 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 1i from 150 mg (0.31 mmol) (R)-2-(4-hydroxy-3,5-dimethyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate and 62 mg (0.34 mmol) 1-methyl-[4,4′]bipiperidinyl. | Cc1cc(C[C@@H](OC(=O)N2CCC(N3CCc4ccccc4NC3=O)CC2)C(=O)N2CCC(C3CCN(C)CC3)CC2)cc(C)c1O | null | null | null |
903,637 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [C:1](=[O:12])([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])OC(C)(C)C.[CH2:13]([O:15][CH:16]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][NH:35][CH3:36])[CH:29]=2)=[CH:24][CH:23]=1)[C:17]([O:19][CH3:20])=[O:18])[CH3:14].C(N(CC)CC)C>ClCCl>[C:8]([O:7][C:1]([CH2:36][NH:35][CH2:34][C:30]1[CH:... | CCOC(Cc1ccc(-c2cccc(CNC)c2)cc1)C(=O)OC | CC(C)(C)OC(=O)OC(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 48 | A solution of 0.4 g (1.9 mmol) of di-tert-butyl carbonate in 5 ml of dichloromethane is added dropwise to a solution of 0.6 g (1.9 mmol) of methyl 2-ethoxy-3-(3′-methylaminomethylbiphenyl-4-yl)propionate and 0.25 ml (1.9 mmol) of triethylamine in 10 ml of dichloromethane. After stirring at room temperature for 48 hours... | CCOC(Cc1ccc(-c2cccc(CNCC(=O)OC(C)(C)C)c2)cc1)C(=O)OC | null | 96 | null |
76,082 | ord_dataset-8868acadaee548d5802e504148fc3b63 | null | 1981-01-01T00:01:00 | true | [Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:36]=[CH:35][C:22]([C:23]([N:25]2[CH:29]([C:30]([O:32]CC)=[O:31])[CH2:28][S:27][CH2:26]2)=[O:24])=[CH:21][CH:20]=1>C(=O)(O)[O-].[Na+].CC(C)=O>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][... | CCOC(=O)C1CSCN1C(=O)c1ccc(NCCCCCCCCCCCCCCCCBr)cc1 | null | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | One-tenth mole of 4-(16-bromohexadecylamino)benzoyl chloride hydrochloride in methylene chloride is added to a solution of 0.1 mole of ethyl thiazolidine-4-carboxylate in chloroform containing two equivalents of triethylamine. After 5 hours at 20° C. the solution is filtered and evaporated to a white solid which is rec... | O=C(O)C1CSCN1C(=O)c1ccc(NCCCCCCCCCCCCCCCCBr)cc1 | null | null | null |
1,063,192 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [OH:1][C:2]1[CH:36]=[CH:35][C:5]([C:6]([CH2:8][NH:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=2[CH:18]2[CH2:27][CH2:26][C:25]3[CH:24]=[C:23]([O:28]C(=O)C(C)(C)C)[CH:22]=[CH:21][C:20]=3[CH2:19]2)=O)=[CH:4][CH:3]=1.Cl[CH2:38][C:39]([N:41]([CH3:43])[CH3:42])=O>>[CH3:42][N:41]([CH3:43])[CH2:39][CH2:38][O:1... | COc1ccc(C2CCc3cc(OC(=O)C(C)(C)C)ccc3C2)c(NCC(=O)c2ccc(O)cc2)c1 | CN(C)C(=O)CCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Synthesized from pivalic acid 6-{2-[(4-hydroxybenzoyl)methylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (25 mg) and 2-chloro-N,N-dimethylacetamide (13 mg) according to an analogous synthetic method to Example 404 and purified by LC-MS, the title compound (5.4 mg) was obtained. | COc1ccc(C2CCc3cc(O)ccc3C2)c(NCCc2ccc(OCCN(C)C)cc2)c1 | null | 22.9 | null |
266,951 | ord_dataset-134cf2fa32ab464880d75db06c38f35a | null | 1993-01-01T00:05:00 | true | [NH2:1][C:2]1[C:3]([F:16])=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([O:12][CH2:13][CH3:14])[C:6]=2[CH:15]=1.[C:17]1([CH3:24])[C:18]([CH3:23])=[CH:19][CH:20]=[CH:21][CH:22]=1>>[CH2:13]([O:12][N:7]1[C:6]2[CH:15]=[C:2]([N:1]3[CH:23]=[C:18]4[C:17]([CH2:22][CH2:21][CH2:20][CH2:19]4)=[CH:24]3)[C:3]([F:16])=[CH:4][C:5]=2[... | CCON1C(=O)COc2cc(F)c(N)cc21 | Cc1ccccc1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0.25 | A mixture consisting of 6-amino-4-ethoxy-7-fluoro-1,4-benzoxazin-3(4H)-one (1.06 g), 1,2-cyclohexanedicarboxyaldehyde (0.7 g) and xylene (50 ml) was stirred for 15 minutes under heat-refluxing. After the solvent had been distilled off under reduced pressure, the residue was purified through silica-gel chromatography (e... | CCON1C(=O)COc2cc(F)c(-n3cc4c(c3)CCCC4)cc21 | null | null | null |
1,534,805 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:10]=[C:11]([C@H:17]2[CH2:21][CH2:20][CH2:19][N:18]2C(OC(C)(C)C)=O)[C:12]([O:15][CH3:16])=[N:13][CH:14]=1>C(Cl)Cl>[F:8][C:9]1[CH:10]=[C:11]([C@H:17]2[CH2:21][CH2:20][CH2:19][NH:18]2)[C:12]([O:15][CH3:16])=[N:13][CH:14]=1 | COc1ncc(F)cc1[C@H]1CCCN1C(=O)OC(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 25 | 1 | A DCM (12 mL) solution of TFA (11.3 mL, 146 mmol) was added to (R)-tert-butyl 2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidine-1-carboxylate (4.33 g, 14.6 mmol) and stirred at ambient temperature for 1 hour. The reaction was then concentrated, taken up in EtOAc, then washed with NaHCO3 and brine. The organic phase was dri... | COc1ncc(F)cc1[C@H]1CCCN1 | null | 48.9 | null |
683,507 | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | null | 2005-01-01T00:09:00 | true | [F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].N1C=CC=CC=1.O[CH2:23][C:24]([CH3:46])([CH3:45])[O:25][C:26]1[C:27]([CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[C:28]2[C:33](=[CH:34][CH:35]=1)[C:32](=[O:36])[CH2:31][CH2:30][CH2:29]2>ClCCl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][CH... | O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F | CC(C)(CO)Oc1ccc2c(c1CCc1ccccc1)CCCC2=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | ClCCl | null | null | null | null | null | null | null | null | null | 0 | 0.25 | Trifluoromethanesulfonic anhydride (0.12 mL, 0.74 mmol) was added to a solution of pyridine (0.14 mL, 1.77 mmol) in dichloromethane (0.5 mL). The resulting mixture was added over 15 min to an ice-cooled solution of 6-(2-hydroxy-1,1-dimethylethoxy)-5-(2-phenylethyl)-3,4-dihydro-1(2H)-naphthalenone (100 mg, 0.30 mmol) in... | CC(C)(COS(=O)(=O)C(F)(F)F)Oc1ccc2c(c1CCc1ccccc1)CCCC2=O | null | 90 | null |
1,233,343 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [Br:1][C:2]1[CH:14]=[CH:13][C:5]2[NH:6][C:7](=O)[O:8][C:9]([CH3:11])([CH3:10])[C:4]=2[CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:24])=CC=1>>[Br:1][C:2]1[CH:14]=[CH:13][C:5]2[NH:6][C:7](=[S:24])[O:8][C:9]([CH3:11])([CH3:10])[C:4]=2[CH:3]=1 | CC1(C)OC(=O)Nc2ccc(Br)cc21 | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The product was prepared, from 6-bromo-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one and Lawesson's reagent using the procedure of Example 9, as a white solid: mp 221-222.5° C.; 1H-NMR (CDCl3) δ 9.38 (s, 1H, D2O exchangeable), 7.42 (dd, 1H, J=8.5, 2.1 Hz), 7.29 (d, 1H, J=2.0 Hz), 6.76 (d, 1H, J=8.4 Hz), 1.76 (s, 6... | CC1(C)OC(=S)Nc2ccc(Br)cc21 | null | null | null |
828,267 | ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f | null | 2008-01-01T00:07:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH:11]([CH2:13]S([O-])(=O)=O)[O:10][N:9]=2)=[CH:4][C:3]=1[F:18].[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C>[N:19]([CH2:13][CH:11]1[O:10][N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([F:18])[CH:4]=2)[CH2:12]1)=[N+:20]=[N-:21] | O=S(=O)([O-])CC1CC(c2ccc(Br)c(F)c2)=NO1 | [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 | null | null | null | null | null | null | null | null | null | null | 80 | 5 | [3-(4-Bromo-3-fluorophenyl)-4,5-dihydroisoxazol-5-yl]methane sulfonate (9.85 g, 28 mmol) was dissolved in dry DMF (100 ml). Sodium azide (2.73 g, 42 mmol) was added and the reaction mixture stirred at 80° C. for 5 hours. The reaction mixture was concentrated in vacuo then azeotroped with xylene (20 ml). The crude produ... | [N-]=[N+]=NCC1CC(c2ccc(Br)c(F)c2)=NO1 | null | 96.1 | null |
142,702 | ord_dataset-84dc0c9e5fb4424687194ef8d14d1c22 | null | 1986-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15](Cl)=[O:16])=[CH:10][C:9]=2[CH3:18])=[O:7])=[CH:4][CH:3]=1.[O-2].[Mg+2].[NH2:23][C@H:24]([C:30]([OH:32])=[O:31])[CH2:25][CH2:26][C:27](=[O:29])[NH2:28].Cl>O1CCOCC1.O>[OH2:7].[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:... | Cc1cc(CC(=O)Cl)n(C)c1C(=O)c1ccc(Cl)cc1 | NC(=O)CC[C@H](N)C(=O)O | null | Cl | [Mg+2] | [O-2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | 25 | 64 | A solution of 30.5 g (0.1 mole) of [5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-yl]-acetyl chloride in 150 ml of dioxane was added slowly at 0°-5° C. to a suspension of 5.88 g (0.15 mole) of magnesium oxide and 14.3 g (0.1 mole) of L-glutamine in 300 ml of water. The resulting yellow suspension was stirred at room tem... | Cc1cc(CC(=O)N[C@@H](CCC(N)=O)C(=O)O)n(C)c1C(=O)c1ccc(Cl)cc1 | null | 20.6 | null |
553,230 | ord_dataset-ec9decb576c4424c9685993f6262bd9c | null | 2002-01-01T00:07:00 | true | [C:1]([C:3]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[NH:5][C:4]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)#[N:2].C([O-])(O)=[O:22].[Na+]>S(=O)(=O)(O)O>[NH2:2][C:1]([C:3]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)[NH:5][C:4]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:... | O=C([O-])O | Cc1c(-c2ccncc2)[nH]c(-c2ccncc2)c1C#N | null | O=S(=O)(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 | 85 | 15 | 3-Cyano-4-methyl-2,5-di(4-pyridyl)-1H-pyrrole (200 mg, 0.77 mmol) was dissolved in sulfuric acid (3 mL) and the mixture was stirred for 15 hours at 85° C. After cooling, fuing sulfuric acid (1 drop) was added to the reaction mixture and stirred for 1 hour at room temperature. The reaction mixture was neutralized by sat... | Cc1c(-c2ccncc2)[nH]c(-c2ccncc2)c1C(N)=O | null | 51 | null |
1,084,360 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [CH2:1]([O:8][C:9]1[C:10]([CH2:15][NH2:16])=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.[CH:22](O)=O>>[CH2:1]([O:8][C:9]1[C:10]2[N:11]([CH:22]=[N:16][CH:15]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | O=CO | NCc1ncccc1OCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=P(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | This compound is prepared according to the same procedure as in preparation II (stage C) from 2.8 g (13.25 mmol) of 1-[3-(benzyloxy)pyridin-2-yl]methanamine [described in Inorg. Chem., (2003), 42(14), 4401] by formylation with formic acid and then cyclization by reaction with phosphoryl chloride. 1.74 g of a brown oil ... | c1ccc(COc2cccn3cncc23)cc1 | null | null | null |
1,642,528 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | C([O:8][CH2:9][CH:10]1[CH2:17][CH2:16][CH2:15][CH2:14][C:11]21[CH2:13][CH2:12]2)C1C=CC=CC=1.[H][H]>CO.CCOC(C)=O>[CH2:12]1[C:11]2([CH2:14][CH2:15][CH2:16][CH2:17][CH:10]2[CH2:9][OH:8])[CH2:13]1 | [H][H] | c1ccc(COCC2CCCCC23CC3)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CO | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of 4-((benzyloxy)methyl)spiro[2,5]-octane (0.42 g, 1.8 mmol) in a 5:1 MeOH-EtOAc (12 mL) Pd/C (0.05 g, 5 wt %, 50% wet Degussa type) was added. The flask was fitted with a balloon of hydrogen, and the heterogeneous reaction mixture was stirred for 2 hours under a hydrogen atmosphere at rt. The catalyst so... | OCC1CCCCC12CC2 | null | null | null |
773,515 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | C(ON[C:10]([C@H:12]1[C@@H:17]([OH:18])[C@H:16]([OH:19])[C@@H:15]([OH:20])[CH2:14][N:13]1[S:21]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][O:33][CH2:34][CH3:35])=[CH:26][CH:25]=1)(=[O:23])=[O:22])=[O:11])C1C=CC=CC=1.C[OH:37]>[Pd]>[CH2:34]([O:33][CH2:32][CH2:31][O:30][C:27]1[CH:26]=[CH:25][C:24]([S:21]([N:13]2[C... | CCOCCOc1ccc(S(=O)(=O)N2C[C@H](O)[C@@H](O)[C@H](O)[C@@H]2C(=O)NOCc2ccccc2)cc1 | CO | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 40 | 1 | The above compound (6) (1.66 g) was dissolved in methanol (70 mL) and 10% Pd—C (350 mg) was added, and then the mixture was stirred under a hydrogen atmosphere at 40° C. for one hour. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by s... | CCOCCOc1ccc(S(=O)(=O)N2C[C@H](O)[C@@H](O)[C@H](O)[C@@H]2C(=O)O)cc1 | null | null | null |
990,893 | ord_dataset-b6d8835b0c934476a36e6149e7597487 | null | 2010-01-01T00:09:00 | true | [C:1]1([CH2:7][CH2:8][C:9](Cl)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([C:20]2([OH:26])[CH2:25][CH2:24][CH2:23][NH:22][CH2:21]2)[CH:17]=[CH:18][CH:19]=1>>[OH:26][C:20]1([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([O:13][CH3:12])[CH:15]=2)[CH2:25][CH2:24][CH2:23][N:22]([C:9](=[O:10])[CH2:8... | O=C(Cl)CCc1ccccc1 | COc1cccc(C2(O)CCCNC2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The compound of Example 53 was prepared according to the general preparation protocol A from 3-phenyl-propionyl chloride and 3-(3-methoxy-phenyl)-piperidine-3-ol. | COc1cccc(C2(O)CCCN(C(=O)CCc3ccccc3)C2)c1 | null | null | null |
1,100,622 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | [CH2:1]([O:4][C:5]1[C:13]([CH3:14])=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][C:6]=1[CH3:15])[CH:2]=[CH2:3].S(Cl)([Cl:18])=O>C(Cl)(Cl)Cl>[CH2:1]([O:4][C:5]1[C:13]([CH3:14])=[CH:12][C:8]([C:9]([Cl:18])=[O:10])=[CH:7][C:6]=1[CH3:15])[CH:2]=[CH2:3] | O=S(Cl)Cl | C=CCOc1c(C)cc(C(=O)O)cc1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of 4-allyloxy-3,5-dimethyl-benzoic acid (5.26 g, 25.5 mmol) in CHCl3 (75 mL), thionylchloride (7.5 mL, 103 mmol) is added at rt. The mixture is refluxed for 2 h before the solvent is evaporated to give crude 4-allyloxy-3,5-dimethyl-benzoic acid chloride as a brownish oil. To a solution of the acid chlorid... | C=CCOc1c(C)cc(C(=O)Cl)cc1C | null | null | null |
110,497 | ord_dataset-406d20cb3f314e2c967b14f55925f895 | null | 1983-01-01T00:10:00 | true | C([O:3][C:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][C:7]2[CH:15]=[C:16]([CH2:19][C:20]([O:22]CC)=[O:21])[CH:17]=[CH:18][C:6]=2[CH:5]=1)C.Br>C1(C)C(C)=CC=CC=1>[O:3]=[C:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][C:7]2[CH:15]=[C:16]([CH2:19][C:20]([OH:22])=[O:21])[CH:17]=[CH:18][C:6]=2[CH2:5]1 | CCOC(=O)Cc1ccc2c(c1)Cc1ccccc1C(OCC)=C2 | null | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1C | null | null | null | null | null | null | null | null | null | null | null | null | In 1 ml of xylene was dissolved 0.1 g of ethyl 10-ethoxy-5H-dibenzo[a,d]cycloheptene-3-acetate obtained in Example 13, and 5 ml of 47% hydrobromic acid was added. The mixture was heated under reflux for 2 hours with vigorous stirring. After the reaction, the reaction mixture was cooled, and then worked up in the same w... | O=C(O)Cc1ccc2c(c1)Cc1ccccc1C(=O)C2 | null | 84.7 | null |
1,708,953 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [F:1][CH:2]([F:15])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:14])=[C:9]([C:11](=O)[CH3:12])[CH:10]=1.[CH3:16][C:17]([S@:20]([NH2:22])=[O:21])([CH3:19])[CH3:18]>>[F:1][CH:2]([F:15])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:14])=[C:9]([CH:11]([NH:22][S@@:20]([C:17]([CH3:19])([CH3:18])[CH3:16])=[O:21])[CH3:12])[CH:10]=1 | CC(C)(C)[S@](N)=O | CC(=O)c1cc(OCC(F)F)ccc1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound is prepared in 61% yield (400 mg, clear colorless oil) from 1-(5-(2,2-difluoroethoxy)-2-methylphenyl)ethanone (440 mg, 2.1 mmol, Step-4) and (R)-2-methylpropane-2-sulfinamide by the similar manner in Step-4 of Amine-1. | Cc1ccc(OCC(F)F)cc1C(C)N[S@](=O)C(C)(C)C | null | 61 | null |
1,428,896 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | Cl.[NH2:2][CH2:3][CH2:4][N:5]1[C:9]([C:10](OCC)=[O:11])=[CH:8][C:7]2[CH2:15][C:16]([CH3:19])([CH3:18])[CH2:17][C:6]1=2.[O-]CC.[Na+]>C(O)C>[CH3:18][C:16]1([CH3:19])[CH2:15][C:7]2[CH:8]=[C:9]3[N:5]([CH2:4][CH2:3][NH:2][C:10]3=[O:11])[C:6]=2[CH2:17]1 | CCOC(=O)c1cc2c(n1CCN)CC(C)(C)C2 | null | null | CC[O-] | Cl | [Na+] | 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 | 55 | null | A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet was purged with nitrogen and charged with crude 110d (˜18 mmol), sodium ethoxide (6.2 g, 92 mmol) and ethanol (120 mL). The mixture was stirred at 55° C. over night. After that time, the reaction mixture was concentrated under... | CC1(C)Cc2cc3n(c2C1)CCNC3=O | null | 23.1 | null |
1,580,601 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [C:1]([O:5][C:6]([N:8]([C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[CH:16][N:17]2[CH2:22][C:23]([OH:25])=[O:24])[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:26][C:27]1[CH:28]=[N+:29]([O-:52])[CH:30]=[C:31]([Cl:51])[C:32]=1[CH2:33][C@@H:34]([C:36]1[CH:41]=[CH:40][C:39]([O:42][CH:43]([F:4... | [O-][n+]1cc(Cl)c(C[C@H](O)c2ccc(OC(F)F)c(OCC3CC3)c2)c(Cl)c1 | CC(C)(C)OC(=O)N(c1cccc2c1ccn2CC(=O)O)S(C)(=O)=O | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | ClCCl | null | null | null | null | null | null | null | null | null | null | null | To a solution of 2-(4-(N-(tert-butoxycarbonyl)methylsulfonamido)-1H-indol-1-yl)acetic acid (250 mg, 0.679 mmol) in DCM (10 ml), (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (285 mg, 0.679 mmol), EDC (390 mg, 2.036 mmol) and DMAP (41.5 mg, 0.339 mmol) were adde... | CC(C)(C)OC(=O)N(c1cccc2c1ccn2CC(=O)O[C@@H](Cc1c(Cl)c[n+]([O-])cc1Cl)c1ccc(OC(F)F)c(OCC2CC2)c1)S(C)(=O)=O | null | 80.3 | null |
879,064 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | C(N1C2=NC=C(C(O)=O)[C:11]([N:12](C)[CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=C2C=N1)C.[C:23]([NH:26][NH:27][C:28]([C:30]1[C:31](NC2CCCC2)=[C:32]2[CH:38]=[N:37][N:36]([CH2:39][CH3:40])[C:33]2=[N:34][CH:35]=1)=[O:29])(=[O:25])[CH3:24]>>[C:23]([NH:26][NH:27][C:28]([C:30]1[CH:31]=[C:32]2[C:38]([N:12]([CH3:11])[CH:13... | CCn1ncc2c(N(C)C3CCOCC3)c(C(=O)O)cnc21 | CCn1ncc2c(NC3CCCC3)c(C(=O)NNC(C)=O)cnc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Intermediate 53 was prepared from Intermediate 52 using an analogous method to that for Intermediate 4. LCMS showed MH+=361; TRET=1.91 min. | CCn1nc(N(C)C2CCOCC2)c2cc(C(=O)NNC(C)=O)cnc21 | null | null | null |
987,349 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[N:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=2)[C@@H:9]([NH:18][C:19]2[N:24]=[C:23]([CH2:25][C:26]3[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=3)[C:22]([N:40]3[CH2:45][CH2:44][CH:43]([C:46]([O:48]CC)=[O:47])[CH2:42][CH2:41]3)=[CH... | CCOC(=O)C1CCN(c2cnc(N[C@H]3C[C@@H](CC)N(C(=O)OCC)c4ccc(OC)nc43)nc2Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC1 | null | null | Cl | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CCO | null | null | null | null | null | null | null | null | null | 50 | null | To a solution of (2R*,4S*)-4-{[3,5-bis(trifluoromethyl)benzyl]-[5-(4-ethoxycarbonylpiperidin-1-yl)pyrimidin-2-yl]}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (245 mg) in ethanol (2 ml) is added aqueous 2N-potassium hydroxide solution (0.332 ml) and the mixture is heated under... | CCOC(=O)N1c2ccc(OC)nc2[C@@H](Nc2ncc(N3CCC(C(=O)O)CC3)c(Cc3cc(C(F)(F)F)cc(C(F)(F)F)c3)n2)C[C@H]1CC | null | 89.1 | null |
217,935 | ord_dataset-67ed03c283094854909157b1038e38e3 | null | 1990-01-01T00:10:00 | true | [Br-:1].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10](O[P+](N(CC)CC)(N(CC)CC)N(CC)CC)[C:11]([F:14])([F:13])[F:12])=[CH:6][CH:5]=1>C(C(C)=O)C(C)C>[Br:1][CH:10]([C:7]1[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=1)[C:11]([F:14])([F:13])[F:12] | CCN(CC)[P+](OC(c1ccc(OC)cc1)C(F)(F)F)(N(CC)CC)N(CC)CC | [Br-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)CC(C)C | null | null | null | null | null | null | null | null | null | null | null | null | In a round-bottom flask equipped with reflux condenser, 53.2 g (0.1 mol) [1-(4-methoxyphenyl)-2,2,2-trifluoroethoxy]tris(diethylamino)phosphonium bromide (product from Example 5) were refluxed in 80 ml of methyl isobutyl ketone for 10 minutes. The subsequent distillation gave 22.2 g (83% of yield) of 1-(1-bromo-2,2,2-t... | COc1ccc(C(Br)C(F)(F)F)cc1 | null | 82.5 | null |
708,196 | ord_dataset-c8069773c1a148aca8ab417108daacc5 | null | 2006-01-01T00:05:00 | true | [Cl:1]N1C(=O)CCC1=O.[Br:9][C:10]([F:25])([F:24])[C:11]([C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1)([F:16])[C:12]([F:15])([F:14])[F:13]>C(#N)C>[Cl:1][C:22]1[CH:23]=[C:17]([C:11]([F:16])([C:12]([F:15])([F:14])[F:13])[C:10]([Br:9])([F:24])[F:25])[CH:18]=[CH:19][C:20]=1[NH2:21] | Nc1ccc(C(F)(C(F)(F)F)C(F)(F)Br)cc1 | O=C1CCC(=O)N1Cl | null | null | 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 | null | 18.24 g (0.14 mol) of N-chlorosuccinimide were added at 60° C. to a mixture of 40.0 g (0.12 mol) of 4-(1-bromo-1,1,2,3,3,3-hexafluoro-2-propyl)aniline from Example 6 and 125 ml of acetonitrile, and the resulting mixture was heated to reflux for 3 hours. Subsequently, the solvent was for the most part distilled off, the... | Nc1ccc(C(F)(C(F)(F)F)C(F)(F)Br)cc1Cl | null | null | null |
728,650 | ord_dataset-eb4226b4f7644a01a737e7547b70014a | null | 2006-01-01T00:09:00 | true | [CH3:1][N:2]([CH3:20])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[CH:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([CH3:32])[CH3:31])[C:25]=1[N:33]=[C:34]=[O:35])([CH3:23])[CH3:22]>>[CH:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30](... | CC(C)c1cccc(C(C)C)c1N=C=O | CCOc1ccc(NCc2ccc(N(C)C)cc2)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 | By the reaction and treatment in the same manner as in Example 2 using [(4-dimethylaminophenyl)methyl](4-ethoxyphenyl)amine (1.0 g) and 2,6-diisopropylphenyl isocyanate (0.89 g) as starting materials, N′-(2,6-diisopropylphenyl)-N-[(4-dimethylaminophenyl)methyl]-N-(4-ethoxyphenyl)urea (0.93 g) was obtained. | CCOc1ccc(N(Cc2ccc(N(C)C)cc2)C(=O)Nc2c(C(C)C)cccc2C(C)C)cc1 | null | 53.1 | null |
118,125 | ord_dataset-3708161f4ba04e959b9a7a8d59fd86e1 | null | 1984-01-01T00:05:00 | true | Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[O:13][N:12]=[C:11]([CH3:14])[CH:10]=1.[Na].[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)([O-:18])=[O:17].[I-].[Na+]>O1CCCC1>[CH3:14][C:11]1[CH:10]=[C:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:25][C:22]2[CH:23]=[CH:24][C:19]([N+:16]... | O=[N+]([O-])c1ccc(O)cc1 | Cc1cc(CCCCCCCBr)on1 | null | [I-] | [Na+] | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 80 | null | A mixture of 3.0 g (0.0115 mole) of 5-(7-bromoheptyl)-3-methylisoxazole and 1.85 g (0.0115 mole) of the sodium salt of 4-nitrophenol in 50 ml of dry tetrahydrofuran containing a few crystals of sodium iodide was heated at 80° C. for 24 hours. The reaction mixture was concentrated in vacuo and the residue triturated wit... | Cc1cc(CCCCCCCOc2ccc([N+](=O)[O-])cc2)on1 | null | null | null |
900,489 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [OH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][C:9]=2[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:23])[CH:5]=[CH:6][CH:7]=1.Br[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[CH:33]=1>>[C:24]1([C:22]([C:9]2... | FC(F)(F)c1cccc(CBr)c1 | O=C(c1ccccc1)c1cnc2c(C(F)(F)F)cccc2c1-c1cccc(O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from [4-(3-hydroxyphenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone and 1-Bromomethyl-3-trifluoromethyl-benzene following the procedure of Example 478: MS (ESI) m/z 552. | O=C(c1ccccc1)c1cnc2c(C(F)(F)F)cccc2c1-c1cccc(OCc2cccc(C(F)(F)F)c2)c1 | null | null | null |
1,565,265 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:11][CH:12]([OH:30])[CH2:13][NH:14][C:15](=[O:29])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:17]=1.[CH3:31]C(O)=O.C=O.[BH3-]C#N.[Na+]>CO>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4... | O=C(NCC(O)CN1CCc2ccccc2C1)c1cccc(NC2CCOCC2)c1 | CC(=O)O | null | C=O | [BH3-]C#N | [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 | 20 | 2 | To a solution of N-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)-3-((tetrahydro-2H-pyran-4-yl)amino)benzamide (300 mg, 0.73 mmol) in MeOH (6 mL) was added AcOH (0.05 mL) and HCHO (548 mg, 7.3 mmol, 40% w/w). The mixture was stirred at 20° C. for 2 h. NaBH3CN (276 mg, 4.38 mmol) was added and the resulting mixtu... | CN(c1cccc(C(=O)NCC(O)CN2CCc3ccccc3C2)c1)C1CCOCC1 | null | 33.9 | null |
1,146,725 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[C:7](B(O)O)[CH:6]=[CH:5][N:4]=1.FC(F)(F)S(O[C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH2:20][C@H:21]([N:28]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:22][O:23]2)(=O)=O>>[CH2:36]([N:28]([CH2:29][C:30]1[CH:35]=[CH:34][C... | O=S(=O)(Oc1cccc2c1C[C@H](N(Cc1ccccc1)Cc1ccccc1)CO2)C(F)(F)F | COc1cc(B(O)O)ccn1 | null | null | null | null | null | null | null | 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 as described for Intermediate example I-2 in 100% yield, starting from 2-methoxypyridine-4-boronic acid and (3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.22 (d, 1 H), 7.23-7.34 (m, 8 H), 7.09-7.23 (m, 3 H), 6.96 (dd, 1 ... | COc1cc(-c2cccc3c2C[C@H](N(Cc2ccccc2)Cc2ccccc2)CO3)ccn1 | null | 100 | null |
1,269,445 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [CH2:1]([O:8][C:9]1[CH:23]=[C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21]([CH:32]([CH3:34])[CH3:33])=[CH:20][C:10]=1[C:11]([NH:13][N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=S)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:36][NH2:37]>C(O)C>[CH2:1]([O:8][C:9]1[CH:23]=[C:22]([O:24][CH2... | NN | CC(C)c1cc(C(=S)NN2CCCCC2)c(OCc2ccccc2)cc1OCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | 2,4-bis-benzyloxy-5-isopropyl-N-piperidin-1-yl-thiobenzamide (unpurified product of the previous step: F67-03), ethanol (5 mL), hydrazine monohydrate (0.5 mL) was placed in a test tube and heated for 1.5 hours under reflux. After completing the reaction, the reaction mixture was concentrated under reduced pressure whil... | CC(C)c1cc(C(=NN)NN2CCCCC2)c(OCc2ccccc2)cc1OCc1ccccc1 | null | null | null |
1,663,831 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [CH2:1]([C:3]12[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH:9]1[CH2:8][CH2:7][O:6][C:5]1[CH:18]=[C:19]([NH2:22])[CH:20]=[CH:21][C:4]2=1)[CH3:2].C1C(=O)N([Br:30])C(=O)C1>C1COCC1>[Br:30][C:20]1[C:19]([NH2:22])=[CH:18][C:5]2[O:6][CH2:7][CH2:8][CH:9]3[CH2:10][C:11]4([O:15][CH2:14][CH2:13][O:12]4)[CH2:1... | O=C1CCC(=O)N1Br | CCC12CCC3(CC1CCOc1cc(N)ccc12)OCCO3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 0.08 | A solution of rac-(7aR,11aS)-11a-ethyl-7,7a,8,10,11,11a-hexahydro-6H-spiro[dibenzo[b,d]oxepine-9,2′-[1,3]dioxolan]-3-amine (86, R2=Ethyl) (11.2 g, 37.0 mmol) in THF (370 mL) was cooled to about −10° C. in a salt/ice bath and was then treated with NBS (6.59 g, 37.0 mmol) with stirring for about 5 min. The reaction was q... | CCC12CCC3(CC1CCOc1cc(N)c(Br)cc12)OCCO3 | null | 96.1 | null |
49,634 | ord_dataset-0bb2e99daa66408fb8dbd6a0781d241c | null | 1978-01-01T00:12:00 | true | Cl[C:2]1[N:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][N:8]([CH2:18][CH3:19])[C:6]=2[N:7]=1.[OH:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C1(C)C=CC=CC=1>[OH:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][N:26]([C:2]2[N:3]=[CH:4][C:5]3[C:11](=[O:12])[C:10]([C:1... | CCOC(=O)c1cn(CC)c2nc(Cl)ncc2c1=O | OCCN1CCNCC1 | null | null | 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 | null | null | 5.6 g. of 2-chloro-5-oxo-6-carbethoxy-8-ethyl-5,8-dihydro-pyrido(2,3-d)pyrimidine, 5.2 g. of 1-β-hydroxyethyl piperazine and 50 cm3 of toluene are heated under reflux for 2 hours. After cooling, the solution is filtered to remove the hydrochloride which has precipitated, and the organic solution is diluted with its own... | CCOC(=O)c1cn(CC)c2nc(N3CCN(CCO)CC3)ncc2c1=O | null | 68 | null |
1,402,475 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]([N:14]([C:19]([C:21]2[N:25]([CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH3:31])[C:24]3[CH:32]=[CH:33][C:34]([F:36])=[CH:35][C:23]=3[N:22]=2)=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:11][C@@H:10]([C:37](O)=[O:38])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+:40].N1(O)C2C=CC=CC... | COCCCCn1c(C(=O)N(CC(C)C)[C@H]2C[C@@H](C(=O)O)CN(C(=O)OC(C)(C)C)C2)nc2cc(F)ccc21 | [NH4+] | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 60 | 3 | (3R,5S)-1-(tert-Butoxycarbonyl)-5-[{[5-fluoro-1-(4-methoxybutyl)-1H-benzimidazol-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-3-carboxylic acid (549 mg), 1H-1,2,3-benzotriazol-1-ol ammonium salt (304 mg) and WSC.HCl (288 mg) were dissolved in DMF (5 ml), diisopropylethylamine (517 μl) was added, and the mixture was s... | COCCCCn1c(C(=O)N(CC(C)C)[C@H]2C[C@@H](C(N)=O)CN(C(=O)OC(C)(C)C)C2)nc2cc(F)ccc21 | null | 208 | null |
1,331,070 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH:13]=[N:12][C:11]2[C:6]1=[N:7][CH:8]=[N:9][C:10]=2[NH2:14].[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C=O)C>[N:15]([CH2:2][CH2:3][CH2:4][N:5]1[CH:13]=[N:12][C:11]2[C:6]1=[N:7][CH:8]=[N:9][C:10]=2[NH2:14])=[N+:16]=[N-:17] | [N-]=[N+]=[N-] | Nc1ncnc2c1ncn2CCCCl | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 80 | 24 | A mixture of 9-(3-chloropropyl)adenine (1.9 g, 9 mM) and sodium azide (1.75 g, 27 mM) in DMF was stirred at 80° C. for 24 hours, cooled to room temperature, and filtered. The solid was washed with CH2Cl2. The solvent was removed from the combined filtrates and the residue was taken up in water with sonication. The aque... | [N-]=[N+]=NCCCn1cnc2c(N)ncnc21 | null | 81 | null |
1,243,779 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)[CH3:2].[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[F:22])[CH:17]=O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([N:11]=[CH:17][C:16]2[CH:19]=[CH:20][C:21]([F:22])=[C:14]([Cl:13])[CH:... | O=Cc1ccc(F)c(Cl)c1 | CCOC(=O)c1ccc(N)cc1 | 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 | 25 | null | A mixture solution of 4-amino-benzoic acid ethyl ester (16.5 g, 100 mmol), 3-chloro-4-fluoro-benzaldehyde (16.1 g, 100 mmol) and p-toluenesulfonic acid (384 mg, 2.0 mmol) in toluene (200 mL) was heated to reflux for 12 hours. Then the reaction mixture was cooled to room temperature. The solvent was removed in vacuo and... | CCOC(=O)c1ccc(N=Cc2ccc(F)c(Cl)c2)cc1 | null | 100.7 | null |
1,712,506 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22](C(OC(C)(C)C)=O)[C@H:21]([C:31]([O:33][CH3:34])=[O:32])[CH:20]=[C:19]1[CH3:35])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3]>C(Cl)Cl.[Br-].[Zn+2].[Br-]>[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][NH:22][C@H:21]([C:31]([O:33][CH... | C=CCON([C@H]1CN(C(=O)OC(C)(C)C)[C@H](C(=O)OC)C=C1C)S(=O)(=O)c1ccccc1[N+](=O)[O-] | null | null | [Br-] | [Zn+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 8 | To a solution of (2S,5R)-1-tert-butyl 2-methyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-methyl-5,6-dihydropyridine-1,2(2H)-dicarboxylate (Intermediate 27, 2.06 g, 4.03 mmol) in DCM (20 mL) at room temperature was added zinc bromide (0.648 mL, 12.08 mmol). After stirring overnight, the reaction mixture was diluted wi... | C=CCON([C@H]1CN[C@H](C(=O)OC)C=C1C)S(=O)(=O)c1ccccc1[N+](=O)[O-] | null | 99.5 | null |
1,619,716 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [NH2:1][C:2]1[C:3]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=O)=[CH:4][C:5]([Cl:12])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[CH3:22][NH:23][S:24](Cl)(=[O:26])=[O:25].[BH4-].[Na+]>N1C=CC=CC=1>[Cl:12][C:5]1[C:6]2[C:11]([C:2]3[NH:1][S:24](=[O:26])(=[O:25])[N:23]([CH3:22])[CH:13]([C:15]4[CH:20]=[CH:1... | Nc1c(C(=O)c2ccc(F)cc2)cc(Cl)c2cccnc12 | CNS(=O)(=O)Cl | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | In a similar fashion using route 27 general procedure 70, (8-amino-5-chloro-quinolin-7-yl)-(4-fluoro-phenyl)-methanone 400 (105 mg, 0.34 mmol), N-methylsulfamoyl chloride 213 (135 mg, 1.0 mmol) and NaBH4 (14 mg, 0.34 mmol) in pyridine (4 ml) gave the title compound (57 mg, 44%) after purification by preparative HPLC (a... | CN1C(c2ccc(F)cc2)c2cc(Cl)c3cccnc3c2NS1(=O)=O | null | 44.4 | null |
200,367 | ord_dataset-31f00a039ca0424788e5e1970d25a8fd | null | 1989-01-01T00:12:00 | true | F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][C@H:12]1[CH2:17][NH:16][C@@H:15]([CH3:18])[CH2:14][NH:13]1.C(=O)(O)[O-].[Na+]>C(O)CCCC>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:13]2[CH2:14][C@H:15]([CH3:18])[NH:16][CH2:17][C@@H:12]2[CH3:11])=[CH:3][CH:4]=1)([O-:10])=[O:9] | O=[N+]([O-])c1ccc(F)cc1 | C[C@H]1CN[C@@H](C)CN1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 4-fluoronitrobenzene (30.34 g, 0.22 mole), cis-2,5-dimethylpiperazine (25 g, 0.22 mole) and sodium bicarbonate (24 g, 0.28 mole) in n-pentanol (150 ml) was heated under nitrogen at 90°-100° for 18 hours. After filtration, the n-pentanol was removed under reduced pressure and the residue was partitioned bet... | C[C@H]1CN(c2ccc([N+](=O)[O-])cc2)[C@@H](C)CN1 | null | null | null |
1,315,445 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [CH2:1]([NH:4][CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].Cl[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][N:10]=1>C(#N)C.O>[N+:15]([C:12]1[CH:13]=[CH:14][C:9]([N:4]([CH2:5][CH2:6][CH3:7])[CH2:1][CH2:2][CH3:3])=[N:10][CH:11]=1)([O-:17])=[O:16] | CCCNCCC | O=[N+]([O-])c1ccc(Cl)nc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | O | null | null | null | null | null | null | null | null | null | null | null | N,N-dipropylamine (3 ml, 22 mmol) was added to a solution of 2-chloro-5-nitropyridine (500 mg, 3.15 mmol) in acetonitrile (7 ml) and heated to reflux overnight. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was then washed with water, brine and dried. Evaporation to dry... | CCCN(CCC)c1ccc([N+](=O)[O-])cn1 | null | 89.6 | null |
1,767,230 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [C:1]([O:9][CH2:10][C@@H:11]1[CH2:15][C@@H:14]([N:16]=[N+]=[N-])[C@H:13]([N:19]2[C:23]3[N:24]=[C:25]([NH2:29])[NH:26][C:27](=[O:28])[C:22]=3[S:21][C:20]2=[O:30])[O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[C:1]([O:9][CH2:10][C@@H:11]1[CH2:15][C@@H:14]([NH2:1... | [N-]=[N+]=N[C@@H]1C[C@@H](COC(=O)c2ccccc2)O[C@H]1n1c(=O)sc2c(=O)[nH]c(N)nc21 | null | null | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 80 | 1 | To a solution of compound [(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-azido-tetrahydrofuran-2-yl]methyl benzoate (compound 33b, 200 mg, 0.466 mmoL) and triphenylphosphine (364 mg, 1.39 mmoL) in THF (10 mL) was added water (0.5 mL) at room temperature. After being stirred at 80° C. for 1 hour, t... | Nc1nc2c(sc(=O)n2[C@@H]2O[C@H](COC(=O)c3ccccc3)C[C@H]2N)c(=O)[nH]1 | null | 42.6 | null |
462,138 | ord_dataset-5ca9db262dd24c5a9315cdc8ef055b7e | null | 2000-01-01T00:04:00 | true | CC(C)(C)C([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[C:15](=[O:33])[NH:16][C:17](=[O:32])[C:18]=2[C:19]2[C:27]3[C:22](=[CH:23][C:24]([N+:28]([O-:30])=[O:29])=[CH:25][CH:26]=3)[N:21]([CH3:31])[CH:20]=2)=[CH:6]1)=O.O(C)[Na]>CO>[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[C:15](=... | Cn1cc(C2=C(c3cn(C(=O)C(C)(C)C)c4ccccc34)C(=O)NC2=O)c2ccc([N+](=O)[O-])cc21 | null | null | CO[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 | 25 | 1 | 1.7 g (3.61 mmol) of 3-[1-(2,2-dimethyl-propionyl)-1H-indol-3-yl]-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione (4) from Step E above in 60 ml of methanol was treated with 5.6 ml (8.96 mmol) of a 1.6 molar solution of NaOCH3 in methanol. The reaction was stirred at room temperature for 1 hour, poured in 2N-HCl/i... | Cn1cc(C2=C(c3c[nH]c4ccccc34)C(=O)NC2=O)c2ccc([N+](=O)[O-])cc21 | null | null | null |
198,351 | ord_dataset-f6fafbb8ce5f4ef099be3a772075ec97 | null | 1989-01-01T00:10:00 | true | [C:1]([N:5]1[C:10](=[O:11])[C:9]([CH3:12])=[C:8](Cl)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[SH-:14].[Na+]>C(O)C>[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH3:12])=[C:8]([SH:14])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2] | [SH-] | Cc1c(Cl)cnn(C(C)(C)C)c1=O | null | [Na+] | 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 | 0 | null | To 75ml of ethanol were added 17.0 g (0.085 mol) of 2-tert.-butyl-5-chloro-4-methyl-3(2H)-pyridazinone and 8.5 g (0.106 mol) of 70% sodium hydrosulfide, and the mixture was stirred under reflux for 4 hours. After cooling, the mixture was poured into 300 ml of ice-water and extracted with 200 ml of ethyl ether. The ethe... | Cc1c(S)cnn(C(C)(C)C)c1=O | null | 96.7 | null |
1,730,595 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | COC1C=CC(C[N:8]([CH2:30][C:31]2[N:32]=[N:33][N:34]([CH3:36])[CH:35]=2)[C:9]2[C:10](=[O:29])[N:11]([CH3:28])[N:12]=[C:13]([O:15][CH2:16][C@H:17]3[CH2:19][C@@H:18]3[C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][N:21]=3)[CH:14]=2)=CC=1.C([O-])(O)=O.[Na+].[C:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45]>>[CH3:27]... | COc1ccc(CN(Cc2cn(C)nn2)c2cc(OC[C@H]3C[C@@H]3c3ccc(OC)cn3)nn(C)c2=O)cc1 | null | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 4-((4-methoxybenzyl)((1-methyl-1H-1,2,3-triazol-4-yl)methyl)amino)-6-(((1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl)methoxy)-2-methylpyridazin-3(2H)-one (55 mg, 0.11 mmol) in TFA (2 mL) was stirred at room temperature for 2 h, then pH was adjusted to 7˜8 with saturated NaHCO3 solution. Extracted with EtOA... | COc1ccc([C@H]2C[C@@H]2COc2cc(NCc3cn(C)nn3)c(=O)n(C)n2)nc1 | null | null | null |
898,234 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | Cl.[N:2]1([C:8]([C:10]2([C:16]#[N:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[CH2:18]([S:21](Cl)(=[O:23])=[O:22])[CH2:19][CH3:20].[OH-].[Na+]>CCN(C(C)C)C(C)C.C(Cl)Cl>[N:2]1([C:8]([C:10]2([C:16]#[N:17])[CH2:15][CH2:14][N:13]([S:21]([CH2:18][CH2:19][CH3:20])(=[O:23])=[O:22])[CH... | CCCS(=O)(=O)Cl | N#CC1(C(=O)N2CCOCC2)CCNCC1 | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of 4-(morpholin-4-ylcarbonyl)piperidine-4-carbonitrile hydrochloride (I-3) (10.40 g, 40 mmole) in DIEA-DCM (1:4, 200 mL) was added n-C3H7SO2Cl (6.28 g, 44 mmole) at 0° C. The resultant mixture was stirred for 1 h at 0° C. After this time, LCMS indicated that the reaction was complete. 2N NaOH (60 mL) was ... | CCCS(=O)(=O)N1CCC(C#N)(C(=O)N2CCOCC2)CC1 | null | null | null |
989,951 | ord_dataset-b6d8835b0c934476a36e6149e7597487 | null | 2010-01-01T00:09:00 | true | C(OC([NH:8][C:9]1[CH:31]=[CH:30][C:12]([O:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]3[CH:20]=[C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N+:24]=4[O-:29])[S:22][C:15]=23)=[C:11]([F:32])[CH:10]=1)=O)(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O.[C:43]1([CH2:49][C:50]([N:52]=[C:53]=[S:54])=[O:51])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>>... | CC(C)(C)OC(=O)Nc1ccc(Oc2ccnc3cc(-c4cccc[n+]4[O-])sc23)c(F)c1 | O=C(Cc1ccccc1)N=C=S | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 25 | 1 | A mixture of 432 (243 mg, 0.53 mmol) in 3:1 mixture of DCM/TFA (8 mL) was stirred at room temperature for 1 hour and concentrated under reduced pressure. The resultant solid was dissolved in 1:1 mixture of EtOH/toluene (10 mL) and treated with 2-phenylacetyl isothiocyanate (140 mg, 0.8 mmol). The reaction mixture was s... | O=C(Cc1ccccc1)NC(=S)Nc1ccc(Oc2ccnc3cc(-c4cccc[n+]4[O-])sc23)c(F)c1 | null | 35.9 | null |
337,229 | ord_dataset-65c44df6676d4ce3a1874db5d7958ca9 | null | 1996-01-01T00:08:00 | true | Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[C:4]([NH:14][CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[N:3]=1.[NH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>>[CH3:17][C:16]([CH3:19])([CH3:18])[CH2:15][NH:14][C:4]1[CH:5]=[C:6]([NH:8][CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])[N:7]=[C:2]([N:... | C1CNCCN1 | CC(C)(C)CNc1cc(NCC(C)(C)C)nc(Cl)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 | The reaction of 2-chloro-4,6-bis(2,2-dimethylpropylamino)pyrimidine with piperazine as described in Example 4 leads to the title product in a yield of 78.3%, m.p.: 132°-136° C. | CC(C)(C)CNc1cc(NCC(C)(C)C)nc(N2CCNCC2)n1 | null | 78.3 | null |
1,515,821 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [OH:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8](=[O:10])[CH3:9])[CH:4]=1.[C:11](=O)([O-])[O-].[Cs+].[Cs+].CI>C1COCC1>[CH3:11][O:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8](=[O:10])[CH3:9])[CH:4]=1 | CC(=O)c1cc(CO)on1 | O=C([O-])[O-] | null | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CI | null | null | null | null | null | null | null | null | null | 60 | null | To a solution of 1-[5-(hydroxymethyl)-1,2-oxazol-3-yl]ethanone (1.00 g, 7.09 mmol) in dry THF (20 mL) under an atmosphere of nitrogen was introduced cesium carbonate (2.31 g, 7.09 mmol) and methyl iodide (5.03 g, 35.43 mmol). The reaction mixture was warmed to 60° C. for 16 hr, cooled to RT and the solids removed by fi... | COCc1cc(C(C)=O)no1 | null | null | null |
1,766,896 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[C:9]2[C:18]3[C:17](=[O:19])[N:16]([CH2:20][CH2:21][CH2:22][O:23][CH:24]4CCCC[O:25]4)[C:15](=[O:30])[N:14]([CH3:31])[C:13]=3[N:12]=[CH:11][C:10]=2[O:32][C:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)=[CH:4][CH:3]=1>C(O)=O.[Zn]>[CH:24]([O:23][CH2:22][CH2:21][CH2:20][N:16]1[C:17](=[... | Cn1c(=O)n(CCCOC2CCCCO2)c(=O)c2c(C(O)c3ccc(Cl)cc3)c(Oc3cccnc3)cnc21 | null | null | [Zn] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=CO | null | null | null | null | null | null | null | null | null | null | 50 | null | To a solution of 5-((4-chlorophenyl)(hydroxy)methyl)-1-methyl-6-(pyridin-3-yloxy)-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (71 mg, 0.128 mmol) in HCOOH (3 mL) was added Zn dust (40.9 mg, 0.641 mmol). The reaction was heated at 50° C. for 2 h, cooled and filtered. The filtrate ... | Cn1c(=O)n(CCCOC=O)c(=O)c2c(Cc3ccc(Cl)cc3)c(Oc3cccnc3)cnc21 | null | 16.7 | null |
851,304 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | [CH3:1][C:2]1([CH3:22])[CH:6]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[C:5]2[C:14]([CH3:21])=[C:15]([NH2:20])[C:16]([CH3:19])=[C:17]([CH3:18])[C:4]=2[O:3]1.[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>C(OCC)(=O)C.CCCCCC>[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH:20][C:15]2[C:16... | Cc1ccc(C2c3c(C)c(N)c(C)c(C)c3OC2(C)C)cc1 | O=C(Cl)c1ccc(F)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CCCCCC | null | null | null | null | null | null | null | null | null | null | null | By using 2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine and 4-fluorobenzoyl chloride, the title compound was synthesized according to Example 1b. Yield: 43%. Melting point: 148-120° C. (Ethyl acetate-hexane) | Cc1ccc(C2c3c(C)c(NC(=O)c4ccc(F)cc4)c(C)c(C)c3OC2(C)C)cc1 | null | 43 | null |
973,820 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | C(O[C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:24])[C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)=[CH:10][C:9]=1[N+:25]([O-])=O)(=O)CC([O-])=O.Cl.[CH3:29][CH2:30][OH:31]>C(Cl)(Cl)Cl>[NH2:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]([C:11]2[CH:10]=[C:9]3[C:8]([CH2:29][C:30](=[O:31])[NH:25]3)=[CH:13][CH:12]=2)=[O:2... | O=C([O-])CC(=O)Oc1ccc(C(=O)c2ccc([N+](=O)[O-])cc2)cc1[N+](=O)[O-] | CCO | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | null | [2-Nitro-4-(4-nitrobenzoyl)phenyl] malonate (4.15 g, 9.61 mmol) was dissolved in EtOH (24 mL) after which Sn powder (9.16 g, 77 mmol) was added followed by dropwise addition of concentrated HCl(aq) (26 mL). The reaction mixture was allowed to reflux for 3 hours, filtered while hot and then allowed to cool to room tempe... | Nc1ccc(C(=O)c2ccc3c(c2)NC(=O)C3)cc1 | null | 51 | null |
433,450 | ord_dataset-386da077ab2340638cada986e2ef0770 | null | 1999-01-01T00:07:00 | true | [NH2:1][C:2]1[N:7]=[C:6]2[C:8]([CH:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)=[CH:9][NH:10][C:5]2=[CH:4][CH:3]=1.[C:18]([C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24])#[N:19]>>[C:18]([C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23]([NH:1][C:2]1[N:7]=[C:6]2[C:8]([CH:11]3[CH2:16][CH2:15... | CN1CCC(c2c[nH]c3ccc(N)nc23)CC1 | N#Cc1cccc(C(=O)Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Beginning with 0.015 gm (0.065 mMol) 5-amino-3-(1-methylpiperidin-4-yl)pyrrolo[3,2-b]pyridine and 0.012 gm (0.072 mMol) 3-cyanobenzoyl chloride, 0.021 gm (92%) of the title compound were prepared essentially by the procedure described in Example 7. | CN1CCC(c2c[nH]c3ccc(NC(=O)c4cccc(C#N)c4)nc23)CC1 | null | 89.9 | null |
971,411 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [Cl:1][C:2]1[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[CH:19][C:3]=1[O:4][C:5]1[CH2:9][N:8]([C@@H:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11]([OH:13])=O)[C:7](=[O:18])[CH:6]=1.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[NH2:46][C:47]1[CH:51]=[CH:50][N:49]([CH2:52][C:53]([CH3:56])([OH:55])[CH3:54])[N:48]=1>ClCCl>[OH:55][C:53]([CH3... | COc1cccc(OC2=CC(=O)N([C@@H](CC(C)C)C(=O)O)C2)c1Cl | CC(C)(O)Cn1ccc(N)n1 | null | CCN=C=NCCCN(C)C | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 2 | A solution of (S)-2-[4-(2-chloro-3-methoxy-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid (200 mg, 0.57 mmol) in dichloromethane (10 mL) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (96 mg, 0.62 mmol) and 1-hydroxybenzotriazole (80 mg, 0.60 mmol). The reaction mixture was stirred at 2... | COc1cccc(OC2=CC(=O)N([C@@H](CC(C)C)C(=O)Nc3ccn(CC(C)(C)O)n3)C2)c1Cl | null | 70.8 | null |
807,187 | ord_dataset-da49b0378abf41bf92ab8ecdd3feb28b | null | 2008-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[C:22]([OH:24])=O)[C:5]([NH:7][CH2:8][C:9]1[NH:13][C:12]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:11]=2[N:10]=1)=[O:6].[N:25]1([CH2:30][CH:31]2[CH2:36][CH2:35][CH2:34][NH:33][CH2:32]2)[CH2:29][CH2:28][CH2:27][CH2:26]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N... | O=C(NCc1nc2cc(Cl)ccc2[nH]1)c1ccc(C(=O)O)c(Cl)c1 | C1CNCC(CN2CCCC2)C1 | null | CN(C)C(On1nnc2ccccc21)=[N+](C)C | F[B-](F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CS(C)=O | null | null | null | null | null | null | null | null | null | null | null | Prepared analogously to Example 1d from 3-chloro-N-(5-chloro-1H-benzimidazol-2-ylmethyl)-4-carboxybenzamide, 3-(pyrrolidin-1-ylmethyl)piperidine, TBTU, and triethylamine in DMSO at ambient temperature. HPLC-MS results: retention time: 3.05 minutes; C26H29Cl2N5O2 (514.45); mass spectrum: (M+H)+=514.2. | O=C(NCc1nc2cc(Cl)ccc2[nH]1)c1ccc(C(=O)N2CCCC(CN3CCCC3)C2)c(Cl)c1 | null | null | null |
1,418,445 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [C:1]1([CH3:18])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:14]=[CH:13][C:12]([C:15]([OH:17])=O)=[CH:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.N=C=N.Cl.Cl.[NH:24]1[C:28]2([CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH2:27][NH:26]/[C:25]/1=[N:34]\[C:35]([C:37]1[C:42]([NH2:43])=[N:41][C:40]([NH2:44])=[C:39]([Cl:45])[N:38]=1)=[O:36].CN1C... | Nc1nc(N)c(C(=O)/N=C2\NCC3(CCNCC3)N2)nc1Cl | Cc1ccc(S(=O)(=O)n2ccc(C(=O)O)c2)cc1 | null | Cl | N=C=N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | CN1CCOCC1 | null | null | null | null | null | null | null | null | null | 25 | null | A solution of 1-(Toluene-4-sulfonyl)-1H-pyrrole-3-carboxylic acid (0.023 g, 0.085 mmol) in NMP (850 l) is added to PS-carbodiimide (190 mg of 1.3 mmol/g loading, 0.24 mmol), followed by a solution of 3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid [1,3,8-triaza-spiro[4.5]dec-(2E)-ylidene]-amide dihydrochloride (Ex. 38)... | Cc1ccc(S(=O)(=O)n2ccc(C(=O)N3CCC4(CC3)CN/C(=N\C(=O)c3nc(Cl)c(N)nc3N)N4)c2)cc1 | null | null | null |
155,187 | ord_dataset-d1c545e3afc447099315419421478aab | null | 1987-01-01T00:03:00 | true | [C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:24][C:14]3=[N:15][C:16](Cl)=[C:17]([N+:20]([O-:22])=[O:21])[C:18](=[O:19])[N:13]3[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH3:25]>C(O)C.CN(C)C=O>[NH2:25][C:16]1[N:15]=[C:14]2[S:24][C:11]([C:8]3[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=3)=[N:12]... | CC(C)(C)c1ccc(-c2nn3c(=O)c([N+](=O)[O-])c(Cl)nc3s2)cc1 | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 1.9 g of 2-(4-tert-butylphenyl)-7-chloro-6-nitro-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one was suspended in a mixture of 20 ml of ethanol and 10 ml of dimethylformamide, and 5 ml of concentrated aqueous ammonia was added dropwise to the suspension while maintaining at a temperature of 60° C. to 70° C. After heating a... | CC(C)(C)c1ccc(-c2nn3c(=O)c([N+](=O)[O-])c(N)nc3s2)cc1 | null | null | null |
1,227,428 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[C:18]([C:19](=[O:25])[C:20]=2[O:21][CH2:22][O:23][CH3:24])=[CH:17][CH:16]=[C:15]([O:26][CH2:27][O:28][CH3:29])[CH:14]=3)=[CH:7][C:6]=1[O:30][CH2:31][O:32][CH3:33].CCN(C(C)C)C(C)C.[CH3:43][C:44]1[CH:49]=[CH:48][C:47]([S:50](Cl)(=[O:52])=[O:51])=[CH:... | Cc1ccc(S(=O)(=O)Cl)cc1 | COCOc1ccc2c(=O)c(OCOC)c(-c3ccc(OCCO)c(OCOC)c3)oc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CCOCC | null | null | null | null | null | null | null | null | null | 25 | 15 | To 2-(4-(2-hydroxyethoxy)-3-(methoxymethoxy)phenyl)-3,7-bis(methoxymethoxy)-4H-chromen-4-one (18 mg, 0.039 mmol) and DIPEA (15 mg, 0.11 mmol) was added 4-methylbenzene-1-sulfonyl chloride (11 mg, 0.058 mmol). The mixture was stirred at rt for 15 h under Ar atmosphere and diluted with ether (30 mL). It was washed with 0... | COCOc1ccc2c(=O)c(OCOC)c(-c3ccc(OCCOS(=O)(=O)c4ccc(C)cc4)c(OCOC)c3)oc2c1 | null | null | null |
1,592,196 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [NH2:1][C:2]1[C:3]([C:10](/[N:12]=[C:13]2/[NH:14][C:15]3([CH2:22][CH2:21][N:20]([C:23]([C:25]4[CH:26]=[C:27]([S:31]([NH:34][CH2:35][CH2:36][C:37]([OH:39])=[O:38])(=[O:33])=[O:32])[CH:28]=[CH:29][CH:30]=4)=[O:24])[CH2:19][CH2:18]3)[CH2:16][NH:17]/2)=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.C(N(CC)C(C)C)(C)C.CN(C... | O=C(CO)N1CCCC1C(F)(F)F | Nc1nc(N)c(C(=O)/N=C2\NCC3(CCN(C(=O)c4cccc(S(=O)(=O)NCCC(=O)O)c4)CC3)N2)nc1Cl | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 0.25 | To a stirred solution of 3-(3-{2-[(E)-3,5-Diamino-6-chloro-pyrazine-2-carbonylimino]-1,3,8-triaza-spiro[4.5]decane-8-carbonyl}-benzenesulfonylamino)-propionic acid (step 2) (400 mg, 0.690 mmol) and N,N-diisopropylethylamine (357 mg, 2.76 mmol) in DMF (4 ml) was added HATU (262 mg, 0.690 mmol). The solution was stirred ... | Nc1nc(N)c(C(=O)/N=C2\NCC3(CCN(C(=O)c4cccc(S(=O)(=O)NCCC(=O)OCC(=O)N5CCCC5C(F)(F)F)c4)CC3)N2)nc1Cl | null | null | null |
1,465,188 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C@H:11]1[CH2:15][NH:14][C@H:13]([C:16]([NH:18][C:19]2([C:22]#[N:23])[CH2:21][CH2:20]2)=[O:17])[CH2:12]1)(=[O:10])=[O:9].[S:24]1[CH2:29][CH2:28][CH:27]([N:30]2[CH2:33][CH2:32][CH:31]2[C:34]([O-])=[O:35])[CH2:26][CH2:25]1.[Li+]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:... | N#CC1(NC(=O)[C@@H]2C[C@@H](S(=O)(=O)c3ccccc3Cl)CN2)CC1 | O=C([O-])C1CCN1C1CCSCC1 | null | [Li+] | null | null | null | null | null | 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 reaction of (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide 7H and lithium 1-(tetrahydro-2H-thiopyran-4-yl)azetidine-2-carboxylate 20J carried out according to the general procedure L yielded (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-(tetrahydro-2H-thiopyran-4... | N#CC1(NC(=O)[C@@H]2C[C@@H](S(=O)(=O)c3ccccc3Cl)CN2C(=O)C2CCN2C2CCSCC2)CC1 | null | null | null |
1,495,729 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])(=O)C.[Na+].[Br:17]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)(=O)C>[Br:17][C:9]1[C:2]([OH:1])=[C:3]([CH:6]=[C:7]([O:10][CH3:11])[CH:8]=1)[CH:4]=[O:5] | BrBr | COc1ccc(O)c(C=O)c1 | null | CC(=O)[O-] | O=S([O-])([O-])=S | [Na+] | 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 | 2 | To 2-hydroxy-5-methoxybenzaldehyde (4.1 mL, 32.86 mmol) in acetic acid (150 mL) were added sodium acetate (4.0 g, 49.3 mmol) and bromine (2.2 mL, 42.7 mmol) and the mixture was stirred at rt for 2 h. Aqueous sodium thiosulfate was added and the mixture was concentrated by rotary evaporation. The solid was dissolved in ... | COc1cc(Br)c(O)c(C=O)c1 | null | 59.9 | null |
358,479 | ord_dataset-58ec5adfcd8648dc9e26ee757d289517 | null | 1997-01-01T00:03:00 | true | [ClH:1].C([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([OH:24])[CH2:17][O:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])=[CH:12][CH:11]=1)C1C=CC=CC=1>[C].[Pd].CO>[ClH:1].[OH:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]([OH:24])[CH2:17][O:18][CH2:19][CH2:20][N:21]([CH3:22])[CH3:23])=[CH:14][CH:15]=1 | CN(C)CCOCC(O)c1ccc(OCc2ccccc2)cc1 | 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 | 2 | A mixture of 2.0 g of 1-(4-benzyloxyphenyl)-2-[2-(N,N-dimethylamino)ethoxy]ethanol hydrochloride, 500 mg of 10% palladium-carbon and 10 ml of methanol was subjected to hydrogenation for 2 hours at room temperature under atmospheric pressure. After the completion of the reaction, palladium-carbon was removed by filtrati... | CN(C)CCOCC(O)c1ccc(O)cc1 | null | 94.1 | null |
904,764 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | C([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])([OH:14])[CH2:10][CH2:9]1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[F:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:15][C:11]1([OH:14])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1 | OC1(Cc2ccccc2F)CCN(Cc2ccccc2)CC1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | A solution of EXAMPLE 1A (39.0 g, 131 mmol) in ethyl acetate (500 mL) was treated with Pd/C (3.90 g), stirred under hydrogen atmosphere (60 psi) until the reaction was complete by TLC analysis, and filtered. The filtrate was concentrated to give a residue that was used without further purification. MS (ESI) m/e 210 (M+... | OC1(Cc2ccccc2F)CCNCC1 | null | null | null |
322,631 | ord_dataset-24ad29d930104afea313b6c3bd11099e | null | 1996-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:17]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[S:18]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[C:6]([CH:16]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[F:15])=[O:8].CO>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:17]([CH2:30][C:31]([O:... | COC(=O)CN(c1ccc(Cl)cc1C(=O)c1ccccc1F)S(=O)(=O)c1ccc([N+](=O)[O-])cc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | The 5-chloro-2'-fluoro-2-[N-(methoxycarbonyl-methyl)-N-(4-nitrophenylsulfonyl)amino]benzophenone prepared in Example 2, step b, is dissolved in 100 ml of ethyl acetate and 5 ml of methanol and hydrogenated at ordinary pressure for 2 hours in the presence of 620 mg of 10% palladium-on-charcoal; the existence of 3 compou... | COC(=O)CN(c1ccc(Cl)cc1C(=O)c1ccccc1F)S(=O)(=O)c1ccc(N)cc1 | null | null | null |
1,330,879 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [N:1]([C@@H:4]1[C:9]([F:11])([F:10])[CH2:8][CH2:7][CH2:6][C@H:5]1[NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[N+]=[N-]>CO>[NH2:1][C@@H:4]1[C:9]([F:11])([F:10])[CH2:8][CH2:7][CH2:6][C@H:5]1[NH:12][C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18] | CC(C)(C)OC(=O)N[C@@H]1CCCC(F)(F)[C@H]1N=[N+]=[N-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 48 | To a clean dry 1 L RBF charged with tert-butyl [(1R,2S)-2-azido-3,3-difluorocyclohexyl]carbamate 27 (18.84 g, 68.2 mmol) was added 400 mL methanol. The system was degassed and purged (3× with N2) before the addition of Pd/C (1.45 g). The reaction was stirred for 2 d under 1 atm of hydrogen. Upon reaction completion, th... | CC(C)(C)OC(=O)N[C@@H]1CCCC(F)(F)[C@H]1N | null | 96.5 | null |
1,223,866 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [C:1](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:2].[Br:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[N:23][C:22]([NH2:28])=[CH:21]2>ClCCl>[Br:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[N:23][C:22]([N:28]=[C:1]=[S:2])=[CH:21]2 | O=c1ccccn1C(=S)n1ccccc1=O | Nc1cc2cc(Br)ccc2cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 3 | To a solution of 1,1′-thiocarbonyldipyridin-2(1H)-one (0.251 g, 1.080 mmol) in dichloromethane at room temperature was added 6-bromoisoquinolin-3-amine (0.241 g, 1.080 mmol). The solution was stirred at room temperature for 3 hours. LC/MS indicated formation of the desired product. The deep orange solution was purified... | S=C=Nc1cc2cc(Br)ccc2cn1 | null | null | null |
233,896 | ord_dataset-45d20d09e4d64f45bdd419044025b4d3 | null | 1991-01-01T00:09:00 | true | [CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:18]=[CH:19][C:20]2[N:21]=[C:22]3[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][N:23]3[CH:29]=2)[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.CN(C)[CH:37]=[O:38]>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:18]=[CH:19][C:20]2[N:21]=[C:22]... | CN(C)C=O | Cc1ccn2cc(C=Cc3ccc([N+](=O)[O-])c(OCc4ccccc4)c3)nc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=P(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 2-[2-(3-benzyloxy-4-nitrophenyl)vinyl]-7-methylimidazo[1,2-a]pyridine (9.00 g) in N,N-dimethylformamide (50 ml), was added dropwise to a solution of phosphorus oxychloride (6.36 ml) in N,N-dimethylformamide (90 ml) at ambient temperature with stirring. After the mixture was stirred for 6 hours, the solven... | Cc1ccn2c(C=O)c(C=Cc3ccc([N+](=O)[O-])c(OCc4ccccc4)c3)nc2c1 | null | null | null |
1,205,157 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [N:1]1[CH:6]=[CH:5][C:4]([C:7](=[N:10][OH:11])[CH2:8][CH3:9])=[CH:3][CH:2]=1.[Li+].CC([N-]C(C)C)C.[C:20]([O:27][CH2:28][CH3:29])(=[O:26])[C:21]([O:23]CC)=O>C1COCC1>[OH:11][N:10]=[C:7]([C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1)[CH:8]([CH3:9])[C:21](=[O:23])[C:20]([O:27][CH2:28][CH3:29])=[O:26] | CCC(=NO)c1ccncc1 | CCOC(=O)C(=O)OCC | null | CC(C)[N-]C(C)C | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0 | 1.5 | 1-(Pyridin-4-yl)propan-1-one oxime (5.3 g, 35.3 mmol) was dissolved in 120 mL of THF and cooled to 0° C. LDA solution (41 mL, 81.3 mmol, 2M in heptane/THF/ethyl benzene) was added dropwise, and the reaction mixture was stirred at 0° C. for 1.5 hour and then warmed to room temperature. The mixture was then transferred t... | CCOC(=O)C(=O)C(C)C(=NO)c1ccncc1 | null | 60 | null |
1,354,393 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | COC1C=CC(C[N:8]2[C:16]3[CH:15]=[CH:14][N:13]=[C:12]([NH:17][CH:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[C:11]=3[C:10]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:9]2)=CC=1.FC(F)(F)S(O)(=O)=O>C(Cl)Cl>[O:24]([C:10]1[C:11]2[C:12]([NH:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[N:13][CH:14]=[CH:15... | COc1ccc(Cn2nc(Oc3ccccc3)c3c(NC4CCOCC4)nccc32)cc1 | null | null | O=S(=O)(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 2 | The crude 1-(4-methoxybenzyl)-3-phenoxy-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[4,3-c]pyridin-4-amine from step 1 was added to methylene chloride (5 mL) and trifluoromethanesulfonic acid (0.5 mL), and the resulting mixture was stirred at room temperature for two hours. The mixture was concentrated under reduced pressu... | c1ccc(Oc2n[nH]c3ccnc(NC4CCOCC4)c23)cc1 | null | null | null |
842,743 | ord_dataset-e2b35e721c2741999b0005d12691f9fe | null | 2008-01-01T00:10:00 | true | [CH2:1]([C:5]1([CH2:19][CH2:20][CH2:21][CH:22]=[CH2:23])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH2:15][O:16][CH3:17])[CH:11]=2)[C:6]1=[O:18])[CH2:2][CH2:3][CH3:4].[CH2:24]([Mg]Br)[CH:25]=[CH2:26]>O1CCCC1>[CH2:1]([C:5]1([CH2:19][CH2:20][CH2:21][CH:22]=[CH2:23])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][C... | C=CC[Mg]Br | C=CCCCC1(CCCC)Cc2cc(OCOC)ccc2C1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | null | A solution of 2-butyl-5-(methoxymethoxy)-2-(4-pentenyl)-1-indanone (400 mg, 1.27 mmol) in anhydrous tetrahydrofuran (THF, 5 mL) was placed under a N2 atmosphere, cooled in a dry ice-acetone bath, stirred, and treated with 2-propenyl magnesium bromide, (1M in THF, 1.9 mL, 1.9 mmol). After warming to room temperature, th... | C=CCCCC1(CCCC)Cc2cc(OCOC)ccc2C1(O)C(=C)C | null | null | null |
1,597,765 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[C:9](F)[N:8]([C@@H:25]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:37][O:38][Na]>CO>[NH2:1][C:2]1[C:3]2[C:10]([C:11... | CO[Na] | CC(C)(C)OC(=O)N1CC[C@@H](n2c(F)c(-c3ccc(Oc4ccccc4)cc3)c3c(N)ncnc32)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 | null | null | To a solution of (R)-tert-butyl 3-(4-amino-6-fluoro-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidine-1-carboxylate (3) (250 mg, 0.51 mmol) in MeOH was added MeONa. The resulting mixture was heated to reflux under N2 overnight. After cooling down to r. t., the reaction mixture was concentrated and the res... | COc1c(-c2ccc(Oc3ccccc3)cc2)c2c(N)ncnc2n1[C@@H]1CCN(C(=O)OC(C)(C)C)C1 | null | 90 | null |
1,586,795 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [Cl:1][C:2]1[N:7]=[C:6]([S:8][C:9]2[CH:10]=[C:11]([NH2:15])[CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[C:16](O)(=[O:19])[CH:17]=[CH2:18]>>[Cl:1][C:2]1[N:7]=[C:6]([S:8][C:9]2[CH:10]=[C:11]([NH:15][C:16](=[O:19])[CH:17]=[CH2:18])[CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1 | C=CC(=O)O | Nc1cccc(Sc2ccnc(Cl)n2)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 a procedure analogous to Example 15, reaction of 3-(2-chloropyrimidin-4-ylthio)benzenamine (300 mg, 1.26 mmol) and acrylic acid (173 μL, 2.52 mmol) furnished the product (250 mg, 68%). | C=CC(=O)Nc1cccc(Sc2ccnc(Cl)n2)c1 | null | 68 | null |
803,022 | ord_dataset-ed846b4b229e4bb09ad9dba95ad7ebeb | null | 2008-01-01T00:01:00 | true | [CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[CH:14]=[C:13]([C:15]([OH:17])=O)[NH:12][C:9]2=[CH:10][N:11]=1.Cl.Cl.[CH:20]([N:23]1[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]1)([CH3:22])[CH3:21].CN(C=O)C.CCN(C(C)C)C(C)C>>[CH:20]([N:23]1[CH2:28][CH2:27][CH:26]([NH:29][C:15]([C:13]2[NH:12][C:9]3=[CH:10][N:11]=[C... | CC(C)N1CCC(N)CC1 | COCCOc1cc2cc(C(=O)O)[nH]c2cn1 | 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 | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 4 | To a solution of 820 mg (3.47 mmol) of 5-(2-Methoxy-ethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid and 745 mg (3.47 mmol) 1-isopropyl-piperidin-4-ylamine dihydrochloride in 30 mL absolute DMF 1.13 g (3.47 mmol) TOTU and 1.81 mL (10.41 mmol) DIPEA were added and the mixture was stirred for 4 h at room temperature. ... | COCCOc1cc2cc(C(=O)NC3CCN(C(C)C)CC3)[nH]c2cn1 | null | null | null |
1,193,258 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | [CH2:1]([O:3][C:4](=[O:42])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16](B3OC(C)(C)C(C)(C)O3)=[CH:15][C:14]=2[CH2:28][N:29]2[C@@H:33]([CH3:34])[C@@H:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[O:31][C:30]2=[O:41])[CH:7]=1)[CH3:2].Br[C:44]1[NH:45][CH:46]=[C:47]([CH3:49])[N:48]=1>>[C... | Cc1c[nH]c(Br)n1 | CCOC(=O)Cc1cccc(Oc2ccc(B3OC(C)(C)C(C)(C)O3)cc2CN2C(=O)O[C@H](c3ccccc3)[C@@H]2C)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 19, Step 3, using the following starting materials: {3-[2-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-phenyl}-acetic acid ethyl ester and 2-bromo-4-methyl-1H-imidazole. | CCOC(=O)Cc1cccc(Oc2ccc(-c3nc(C)c[nH]3)cc2CN2C(=O)O[C@H](c3ccccc3)[C@@H]2C)c1 | null | null | null |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.