Azetidine → HCID 57937367, compound

HRID 1435514Notes

Reaction equation

HRID 1435514 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].[NH:27]1[CH2:30][CH2:29][CH2:28]1>CN(C1C=CN=CC=1)C.CC#N>[N:27]1([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])[CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 2

HCID 10422AzetidineHCID 579372942-tert-Butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 57937367HCID 57937367, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

Following the same procedure in Example 1, Step A, using 2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chloride (122 mg, 0.3 mmol), azetidine (41 uL, 34 mg, 0.6 mmol) and DMAP (73 mg, 0.6 mmol) in MeCN (5 mL). The crude product was purified by MPLC using Hex/EtOAc (1:1) on silica gel to give 88 mg (69%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.49-1.63 (m, 2 H), 1.65 (s, 9 H), 1.69-1.93 (m, 4 H), 1.98-2.19 (m, 4 H), 2.21-2.34 (m, 1 H), 3.73-3.82 (m, 4 H), 4.51 (d, J=7.42 Hz, 2 H), 7.84 (dd, J=8.59, 1.76 Hz, 1 H), 7.98 (d, J=8.59 Hz, 1 H), 8.13 (d, J=1.76 Hz, 1 H); MS (ESI) (M+H)+=426.2.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-368c9fdf079645c596bb32073c117b17
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

Loading…