Triethylamine → Carbamic acid, N-[trans-4-[[(3-chlorobenzo[b]thien-2-yl)carbonyl][[3-(4-pyridinyl)phenyl]methyl]amino]cyclohexyl]-, 1,1-dimethylethyl ester

HRID 885025Notes

Reaction equation

HRID 885025 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[Cl:36][C:37]1[C:38]2[CH:48]=[CH:47][CH:46]=[CH:45][C:39]=2[S:40][C:41]=1[C:42](Cl)=[O:43]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:42]([C:41]2[S:40][C:39]3[CH:45]=[CH:46][CH:47]=[CH:48][C:38]=3[C:37]=2[Cl:36])=[O:43])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5198983-Chlorobenzo(b)thiophene-2-carbonyl chlorideHCID 59201760tert-Butyl ((1r,4r)-4-((3-(pyridin-4-yl)benzyl)amino)cyclohexyl)carbamate

Product 1

HCID 59201762Carbamic acid, N-[trans-4-[[(3-chlorobenzo[b]thien-2-yl)carbonyl][[3-(4-pyridinyl)phenyl]methyl]amino]cyclohexyl]-, 1,1-dimethylethyl esterYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 18 (410 mg, 1.1 mmol) and Et3N (280 μL, 2.0 mmol) in CH2Cl2 (10 mL) was added 3-chlorobenzo[b]thiophene-2-carbonyl chloride 12 (278 mg, 1.2 mmol), and the reaction mixture was stirred at room temperature for 0.5 h. The solvent was removed and the residue was purified by a flash chromatography on silica gel (acetone/PE=5:1) to give the desired product 19 (587 mg) in 96% yield; 1H-NMR (400 MHz, CDCl3): 8.65 (br, 2H), 7.20-8.20 (m, 10H), 3.70-5.00 (m, 4H), 3.20-3.40 (br, 1H), 1.75-2.20 (m, 4H), 1.42-1.75 (br, 2H), 1.38 (s, 9H), 0.90-1.30 (br, 2H); 13C NMR (100 MHz, CDCl3): 163.7, 155.1, 150.2, 148.1, 147.7, 139.2, 138.4, 137.2, 135.6, 130.0, 129.3, 127.6, 126.5, 126.2, 125.5, 122.7, 122.5, 121.6, 119.0, 79.2, 58.7, 48.5, 45.1, 32.1, 30.5, 29.7, 29.3, 28.3; HRMS (EI) calcd for C32H34ClN3O3S (M+) 575.2009; found 575.2018.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by a flash chromatography on silica gel (acetone/PE=5:1)

Sources & evidence

ORD record
ord-7c2ba22258fa4259bfc2cc9e09ed74a2
Source dataset
uspto-grants-2012_08
Patent number
US08242142B2

Reaction notes

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