3-Aminoazetidine, 3-BOC protected → HCID 57937374, compound

HRID 1435507Notes

Reaction equation

HRID 1435507 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][CH:29]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:28]1>CN(C1C=CN=CC=1)C.CC#N>[C:34]([O:33][C:32](=[O:38])[NH:31][CH:29]1[CH2:30][N:27]([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])[CH2:28]1)([CH3:37])([CH3:35])[CH3:36]

Participants

5

Reactant 2

HCID 15194053-Aminoazetidine, 3-BOC protectedHCID 579372942-tert-Butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 57937374HCID 57937374, compoundYield 74%

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 (0.41 g, 1.0 mmol), tert-butyl azetidin-3-ylcarbamate (0.17 g, 1.0 mmol) and DMAP (0.37 g, 3.0 mmol) in MeCN (20 mL). The crude product was purified by MPLC using Hex/EtOAc (1:1) on silica gel to give 0.40 g (74%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.33 (s, 9 H), 1.48-1.62 (m, 2 H), 1.64 (s, 9 H), 1.67-1.87 (m, 4 H), 1.98-2.15 (m, 2 H), 2.19-2.35 (m, 1 H), 3.62 (t, J=7.03 Hz, 2 H), 3.96 (t, J=8.11 Hz, 2 H), 4.05-4.16 (m, 1 H), 4.51 (d, J=7.42 Hz, 2 H), 7.86 (dd, J=9.18, 1.17 Hz, 1 H), 7.98 (d, J=8.79 Hz, 1 H), 8.14 (d, J=1.56 Hz, 1 H); MS (ESI) (M+H)+=541.3; Anal. Calcd for C26H38F2N4O4S+1.00 TFA+0.20 EtOAc (674.72): C, 51.62; H, 6.07; N, 8.30. Found: C, 51.73; H, 5.94; N, 8.27.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-4737db7901284daabe13050d9f0fe534
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

Loading…