Ethylamine → cis-2-[(4-Chlorobenzenesulfonyl)-(4-ethylcarbamoyl-benzyl)-amino]-cycloheptanecarboxylic acid amide

HRID 7048

Reaction equation

HRID 7048 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([C@@H:22]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C@@H:23]2[C:29](=[O:31])[NH2:30])[S:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:6][CH:5]=1.[CH2:33]([NH2:35])[CH3:34]>>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([S:12]([N:11]([CH2:10][C:7]2[CH:6]=[CH:5][C:4]([C:3](=[O:2])[NH:35][CH2:33][CH3:34])=[CH:9][CH:8]=2)[C@H:22]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]2[C:29]([NH2:30])=[O:31])(=[O:13])=[O:14])=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 6341EthylamineHCID 11236936cis-4-[[(2-Carbamoyl-cycloheptyl)-(4-chlorobenzenesulfonyl)-amino]-methyl]-benzoic acid methyl ester

Product 1

HCID 69655987cis-2-[(4-Chlorobenzenesulfonyl)-(4-ethylcarbamoyl-benzyl)-amino]-cycloheptanecarboxylic acid amideYield 18%

Conditions

Temperature
60 °C

Procedure

cis-4-[[(2-Carbamoyl-cycloheptyl)-(4-chlorobenzenesulfonyl)-amino]-methyl]-benzoic acid methyl ester (50 mg, 0.10 mmol) and ethylamine (1.0 M in MeOH, 6 mL) were heated with stirring at 60° C. for 16 h. The solution was concentrated to dryness and the product purified by silica-gel column chromatography (20%–90% EtOAc/Hexanes) to afford 9.0 mg (18% yield) of the titled compound: 1 H NMR (DMSO-d6) δ 7.89 (m, 1 H), 7.80 (d, 2 H, J=8.0 Hz), 7.72 (d, 2 H, J=8.0 Hz), 7.64 (d, 2 H, J=8.0 Hz), 7.36 (d, 2 H, J=8.0 Hz), 7.32 (s br, 1 ), 6.67 (s br, 1 H), 4.58 (AB2,2 H,Δv=16,Jab=108 Hz), 3.97 (m, 1 H), 2.76 (m, 1 H), 2.26 (m, 2 H), 1.72 (m, 2 H), 1.35 (m, 8 H), 1.12 (t, 3 H, J=8.0 Hz); MS m/e 492.29 (M+H)+.

Workup

  1. concentrationThe solution was concentrated to dryness
  2. customthe product purified by silica-gel column chromatography (20%–90% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-075826d4fe38408cb9e4371c687d2ac0
Source dataset
uspto-grants-2006_08
Patent number
US07084178B2

Linked notes

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