4-Chloro-1-ethyl-1H-pyrazole-3-carboxylic acid → 4-Chloro-1-ethyl-1H-pyrazole-3-carboxylic acid [3-((R)-2-amino-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-4-yl)-4-fluoro-phenyl]-amide

HRID 1941863Notes

Reaction equation

HRID 1941863 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]([C@:8]2([CH3:17])[C:13]([F:15])([F:14])[CH2:12][O:11][C:10]([NH2:16])=[N:9]2)[CH:7]=1.[Cl:19][C:20]1[C:21]([C:27](O)=[O:28])=[N:22][N:23]([CH2:25][CH3:26])[CH:24]=1>>[NH2:16][C:10]1[O:11][CH2:12][C:13]([F:14])([F:15])[C@:8]([C:6]2[CH:7]=[C:2]([NH:1][C:27]([C:21]3[C:20]([Cl:19])=[CH:24][N:23]([CH2:25][CH3:26])[N:22]=3)=[O:28])[CH:3]=[CH:4][C:5]=2[F:18])([CH3:17])[N:9]=1

Participants

3

Reactant 2

HCID 5898204-Chloro-1-ethyl-1H-pyrazole-3-carboxylic acidHCID 58304207(R)-4-(5-amino-2-fluoro-phenyl)-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine

Product 1

HCID 532413984-Chloro-1-ethyl-1H-pyrazole-3-carboxylic acid [3-((R)-2-amino-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-4-yl)-4-fluoro-phenyl]-amide

Procedure

The condensation of (R)-4-(5-amino-2-fluoro-phenyl)-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine (intermediate XI-1) and 4-chloro-1-ethyl-1H-pyrazole-3-carboxylic acid (CAS512810-20-7) following procedure I yielded the title compound as a white solid. MS (ISP): m/z=416.3 [M+H]+.

Sources & evidence

ORD record
ord-322b81339a2049c9b0eec05c254502f6
Source dataset
uspto-grants-2013_03
Patent number
US08389513B2

Reaction notes

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