5-Chloro-2-thiophenecarboxylic acid → HCID 72943814, compound

HRID 710199Notes

Reaction equation

HRID 710199 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:22])=[C:6]([C@:8]2([CH3:21])[C@H:13]3[C:14]([F:19])([F:18])[CH2:15][CH2:16][CH2:17][C@H:12]3[O:11][C:10]([NH2:20])=[N:9]2)[CH:7]=1.[Cl:23][C:24]1[S:28][C:27]([C:29](O)=[O:30])=[CH:26][CH:25]=1>>[NH2:20][C:10]1[O:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][C:14]([F:18])([F:19])[C@@H:13]2[C@:8]([C:6]2[CH:7]=[C:2]([NH:1][C:29]([C:27]3[S:28][C:24]([Cl:23])=[CH:25][CH:26]=3)=[O:30])[CH:3]=[CH:4][C:5]=2[F:22])([CH3:21])[N:9]=1

Participants

3

Reactant 2

HCID 950485-Chloro-2-thiophenecarboxylic acidHCID 90021102HCID 90021102, compound

Product 1

HCID 72943814HCID 72943814, compoundYield 72%

Procedure

The coupling of (4S,4aR,8aR)-4-(5-amino-2-fluoro-phenyl)-5,5-difluoro-4-methyl-4a,5,6,7,8,8a-hexahydro-4H-benzo[e][1,3]oxazin-2-ylamine (intermediate XIIIa-2) and 5-chloro-thiophene-2-carboxylic acid (CAS 24065-33-6) following procedure Q yielded the title compound as a white solid (72% yield). MS: m/z=458.3 [M+H]+.

Sources & evidence

ORD record
ord-d23705e8e2894b8abb2112a0a9e6d8c5
Source dataset
uspto-grants-2015_11
Patent number
US09181232B2

Reaction notes

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