Ethanolamine → HCID 57937386, compound

HRID 1435513Notes

Reaction equation

HRID 1435513 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].[CH2:33]([CH2:35][NH2:36])[OH:34]>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][CH2:35][CH2:33][OH:34])=[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 700EthanolamineHCID 86615826HCID 86615826, compound

Product 1

HCID 57937386HCID 57937386, compoundYield 44%

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 ethanolamine (12 uL, 12 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 1.49-1.65 (m, 2 H), 1.68 (s, 9 H), 1.70-1.86 (m, 4 H), 2.02-2.14 (m, 2 H), 2.19-2.36 (m, 1 H), 3.13 (t, J=5.57 Hz, 2 H), 3.48 (t, J=5.57 Hz, 2 H), 3.64 (dd, J=8.50, 6.35 Hz, 2 H), 3.99 (t, J=8.11 Hz, 2 H), 4.17-4.27 (m, 1 H), 4.55 (d, J=7.42 Hz, 2 H), 7.93 (dd, J=8.79, 1.76 Hz, 1 H), 8.06 (d, J=8.79 Hz, 1 H), 8.17 (d, J=1.37 Hz, 1 H); MS (ESI) (M+H)+=528.3; Anal. Calcd for C24H35F2N5O4S+0.90 TFA+1.0H2O+0.10 EtOAc (658.29): C, 47.99; H, 5.93; N, 10.64. Found: C, 47.99; H, 5.95; N, 10.68.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-6a768df2bc6b43ec9c034a82485a834b
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

Loading…