Diisopropylethylamine → HCID 57937371, compound

HRID 1435525Notes

Reaction equation

HRID 1435525 reaction equation
[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13][CH2:12]2)[C:8]2[CH:19]=[CH:20][C:21]([S:23](Cl)(=[O:25])=[O:24])=[CH:22][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[C:36]([O:40][C:41]([NH:43][C@H:44]1[CH2:48][CH2:47][NH:46][CH2:45]1)=[O:42])([CH3:39])([CH3:38])[CH3:37]>C(Cl)Cl>[C:36]([O:40][C:41](=[O:42])[NH:43][C@H:44]1[CH2:48][CH2:47][N:46]([S:23]([C:21]2[CH:20]=[CH:19][C:8]3[N:9]([CH2:10][CH:11]4[CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13][CH2:12]4)[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[N:6][C:7]=3[CH:22]=2)(=[O:25])=[O:24])[CH2:45]1)([CH3:39])([CH3:37])[CH3:38]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 579372942-tert-Butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 57937371HCID 57937371, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the same procedure in Example 1, step A, using 2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chloride (2 g, 5 mmol), N,N-diisopropylethylamine (3.5 mL, 20 mmol) and (3S)-(−)-3-(tert-butoxycarbonylamino)pyrrolidine (1.4 g, 7.5 mmol) in (10 mL) methylene chloride. The crude product was purified by MPLC on silica gel using 8-70% EtOAc/hexane. Yield: 2.77 g (100%). 1H NMR (400 MHz, METHANOL-D4) δ 1.35 (s, 9 H) 1.52 (d, J=11.72 Hz, 4 H) 1.58 (s, 9 H) 1.62-1.73 (m, 4 H) 1.75-1.81 (m, 1 H) 1.93-2.00 (m, 1 H) 3.03-3.10 (m, 1 H) 3.24-3.29 (m, 2 H) 3.35-3.47 (m, 3 H) 4.40 (d, J=7.42 Hz, 2 H) 7.71-7.78 (m, 2 H) 8.09 (d, J=1.37 Hz, 1 H).

Workup

  1. customThe crude product was purified by MPLC on silica gel using 8-70% EtOAc/hexane

Sources & evidence

ORD record
ord-3616b8703886441fbea09903b1195602
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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