3,3-Difluoroazetidine hydrochloride → HCID 178441266, compound

HRID 1888692Notes

Reaction equation

HRID 1888692 reaction equation
[CH2:1]([C:5]1=[CH:6][N:7]([C:24]([CH3:27])([CH3:26])[CH3:25])[S:8]/[C:9]/1=[N:10]\[C:11]([C@:13]1([CH3:23])[CH2:17][CH2:16][C@H:15]([C:18]([OH:20])=O)[C:14]1([CH3:22])[CH3:21])=[O:12])[CH2:2][CH2:3][CH3:4].Cl.[F:29][C:30]1([F:34])[CH2:33][NH:32][CH2:31]1>>[CH2:1]([C:5]1=[CH:6][N:7]([C:24]([CH3:25])([CH3:26])[CH3:27])[S:8]/[C:9]/1=[N:10]\[C:11]([C@:13]1([CH3:23])[CH2:17][CH2:16][C@H:15]([C:18]([N:32]2[CH2:33][C:30]([F:34])([F:29])[CH2:31]2)=[O:20])[C:14]1([CH3:21])[CH3:22])=[O:12])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 27582473,3-Difluoroazetidine hydrochlorideHCID 178441278HCID 178441278, compound

Product 1

HCID 178441266HCID 178441266, compound

Procedure

The product from Example 173 and 3,3-difluoroazetidine hydrochloride (Oakwood) were processed using the method described in Example 178 to afford the title compound. 1H NMR (DMSO-d6) δ 0.51 (s, 3H), 0.90 (t, J=7.3 Hz, 3H), 1.22 (s, 3H), 1.25 (s, 3H), 1.26-1.36 (m, 2H), 1.39-1.48 (m, 1H), 1.57 (s, 9H), 1.57-1.78 (m, 3H), 1.93-2.05 (m, 1H), 2.62-2.67 (m, 2H), 2.73-2.83 (m, 1H), 2.88-2.94 (m, 1H), 4.14-4.37 (m, 2H), 4.41-4.53 (m, 1H), 4.74-4.86 (m, 1H), 8.51 (s, 1H). (ESI+) m/z 470 (M+H)+.

Sources & evidence

ORD record
ord-1041ce7cef6e41b082eb95ad7fe5f3c6
Source dataset
uspto-grants-2013_08
Patent number
US08501794B2

Reaction notes

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