Cyclopentylamine → 4-Chloro-2-(2-cyclopentylamino-acetylamino)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

HRID 1172531Notes

Reaction equation

HRID 1172531 reaction equation
[CH:1]1([NH2:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:7][O:8][C:9]([C:11]1[CH:12]=[C:13]([CH3:34])[C:14]2[O:20][C:19]3[C:21]([Cl:30])=[CH:22][C:23]([NH:25][C:26](=[O:29])[CH2:27]Cl)=[CH:24][C:18]=3[CH2:17][S:16](=[O:32])(=[O:31])[C:15]=2[CH:33]=1)=[O:10]>CN(C=O)C>[CH3:7][O:8][C:9]([C:11]1[CH:12]=[C:13]([CH3:34])[C:14]2[O:20][C:19]3[C:21]([Cl:30])=[CH:22][C:23]([NH:25][C:26](=[O:29])[CH2:27][NH:6][CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)=[CH:24][C:18]=3[CH2:17][S:16](=[O:32])(=[O:31])[C:15]=2[CH:33]=1)=[O:10]

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 116336414-Chloro-2-(2-chloro-acetylamino)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Product 1

HCID 1317285004-Chloro-2-(2-cyclopentylamino-acetylamino)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cyclopentyl amine (0.27 ml, 2.7 mmol) was added to a solution of Example 133 (0.4 g, 0.9 mmol) in DMF (10 mL). The reaction mixture was processed as described in the synthesis of Example 139k to obtain the title compound. Yield: 0.37 g, (83%); 1H NMR (CDCl3): δ 1.38 (m, 2H, CH2), 1.72 (m, 4H, 2CH2), 1.87 (m, 2H, CH2), 2.7 (s, 3H, CH3), 2.96 (s, 1H, NH), 3.15 (m, 1H, CH), 3.38 (s, 2H, CH2), 3.92 (s, 3H, OCH3), 4.7 (s, 2H, CH2), 7.57 (s, 1H, Ar), 7.83 (s, 1H, Ar), 8.1 (s, 1H, Ar), 8.45 (s, 1H, Ar), 9.64 (s, 1H, NH); MS: m/e (ES+) 493 (M+1).

Workup

  1. customas described in the synthesis of Example 139k

Sources & evidence

ORD record
ord-11d8aef34965430da8818cdb7e5d1681
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

Loading…