3,3-Difluoroazetidine hydrochloride → HCID 59543510, compound

HRID 1697729Notes

Reaction equation

HRID 1697729 reaction equation
[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20](F)=[CH:19][C:18]=3[Cl:24])(=[O:16])=[O:15])[CH2:11][N:10]2[C:25]2[N:26]([CH:31]3[CH2:34][CH2:33][CH2:32]3)[N:27]=[C:28]([CH3:30])[CH:29]=2)=[O:8])[CH2:5][CH2:4]1)#[N:2].Cl.[F:36][C:37]1([F:41])[CH2:40][NH:39][CH2:38]1>C(#N)C>[Cl:24][C:18]1[CH:19]=[C:20]([N:39]2[CH2:40][C:37]([F:41])([F:36])[CH2:38]2)[CH:21]=[CH:22][C:17]=1[S:14]([C@H:12]1[CH2:11][N:10]([C:25]2[N:26]([CH:31]3[CH2:34][CH2:33][CH2:32]3)[N:27]=[C:28]([CH3:30])[CH:29]=2)[C@H:9]([C:7]([NH:6][C:3]2([C:1]#[N:2])[CH2:5][CH2:4]2)=[O:8])[CH2:13]1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 27582473,3-Difluoroazetidine hydrochlorideHCID 66770817HCID 66770817, compound

Product 1

HCID 59543510HCID 59543510, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In analogy to the procedure described in example 389, (2S,4R)-4-(2-chloro-4-fluoro-benzenesulfonyl)-1-(2-cyclobutyl-5-methyl-2H-pyrazol-3-yl)-pyrrolidine-2-carboxylic acid (1-cyano-cyclopropyl)-amide (example 385b) was reacted with 3,3-difluoroazetidine hydrochloride (CAS Reg. No. 288315-03-7) in acetonitrile at 90° C. for 48 h to give the title compound as off-white foam. MS (ESI): m/z=579.3 [M+H]+.

Sources & evidence

ORD record
ord-7e6a07beaa034b75a052b7b99847b72f
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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