Cyclopropylamine → HCID 57937387, compound

HRID 1435512Notes

Reaction equation

HRID 1435512 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]([N:26]3[CH2:29][CH:28]([N:30]=[C:31]=[O:32])[CH2:27]3)(=[O:25])=[O:24])=[CH:22][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH:33]1([NH2:36])[CH2:35][CH2:34]1>C1COCC1>[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:12][CH2:13][C:14]([F:17])([F:18])[CH2:15][CH2:16]2)[C:8]2[CH:19]=[CH:20][C:21]([S:23]([N:26]3[CH2:27][CH:28]([NH:30][C:31]([NH:36][CH:33]4[CH2:35][CH2:34]4)=[O:32])[CH2:29]3)(=[O:25])=[O:24])=[CH:22][C:7]=2[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 86615826HCID 86615826, compound

Product 1

HCID 57937387HCID 57937387, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the same procedure in Example 105, Step A, using 2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-5-[(3-isocyanatoazetidin-1-yl)sulfonyl]-1H-benzimidazole (0.095 mmol) and cyclopropylamine (13 uL, 11 mg, 0.19 mmol) in THF (6.0 mL). The crude product was purified by MPLC using EtOAc/MeOH (20:1) on silica gel to give 22 mg (44%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 0.29-0.40 (m, 2 H), 0.57-0.66 (m, 2 H), 1.49-1.64 (m, 2 H), 1.67 (s, 9 H), 1.70-1.86 (m, 4 H), 1.99-2.15 (m, 2 H), 2.20-2.31 (m, 1 H), 2.31-2.41 (m, 1 H), 3.65-3.78 (m, 2 H), 3.94-4.06 (m, 2 H), 4.15-4.30 (m, 1 H), 4.55 (d, J=7.42 Hz, 2 H), 7.92 (dd, J=8.69, 1.66 Hz, 1 H), 8.05 (d, J=8.79 Hz, 1 H), 8.18 (d, J=1.56 Hz, 1 H); MS (ESI) (M+H)+=524.3; Anal. Calcd for C25H35F2N5O3S+1.20 TFA+0.60H2O+0.40 EtOAc (711.33): C, 49.64; H, 5.75; N, 9.85. Found: C, 49.62; H, 5.71; N, 9.83.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-1d2f9596edba46db9882ad1fcd26250b
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

Loading…