3,3-Difluoroazetidine hydrochloride → 5-chloro-N-{3-[(3,3-difluoroazetidin-1-yl)carbonyl]-4-methyl-4,6-dihydrothieno[2,3-c]furan-2-yl}-2-(trifluoromethyl)benzamide

HRID 1015595Notes

Reaction equation

HRID 1015595 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:23]([F:26])([F:25])[F:24])=[C:6]([CH:22]=1)[C:7]([NH:9][C:10]1[S:18][C:13]2[CH2:14][O:15][CH:16]([CH3:17])[C:12]=2[C:11]=1[C:19](O)=[O:20])=[O:8].Cl.[F:28][C:29]1([F:33])[CH2:32][NH:31][CH2:30]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:23]([F:26])([F:24])[F:25])=[C:6]([CH:22]=1)[C:7]([NH:9][C:10]1[S:18][C:13]2[CH2:14][O:15][CH:16]([CH3:17])[C:12]=2[C:11]=1[C:19]([N:31]1[CH2:32][C:29]([F:33])([F:28])[CH2:30]1)=[O:20])=[O:8]

Participants

3

Reactant 2

HCID 27582473,3-Difluoroazetidine hydrochlorideHCID 673006322-{[5-Chloro-2-(trifluoromethyl)benzoyl]amino}-4-methyl-4,6-dihydrothieno[2,3-c]furan-3-carboxylic acid

Product 1

HCID 247725435-chloro-N-{3-[(3,3-difluoroazetidin-1-yl)carbonyl]-4-methyl-4,6-dihydrothieno[2,3-c]furan-2-yl}-2-(trifluoromethyl)benzamide

Procedure

The title compound was prepared from the product of Example 53A and commercially available 3,3-difluoroazetidine hydrochloride by the procedure described for Example 2B. 1H NMR (DMSO-d6, 300 MHz) δ 1.30 (d, J=6.4 Hz, 3H), 4.30-4.53 (m, 4H), 4.89-5.01 (m, 2H), 5.18-5.27 (m, 1H), 7.82-7.95 (m, 3H), 11.60 (br s, 1H). MS (ESI+) m/z 481 (M+H)+. Anal. calcd. for C19H14ClF5N2O3S: C, 47.46; H, 2.93; N, 5.83. Found: C, 47.38; H, 2.52; N, 5.72.

Sources & evidence

ORD record
ord-33ec1223a28e43eba3f9a7a803a76c92
Source dataset
uspto-grants-2011_07
Patent number
US07985768B2

Reaction notes

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