3-Amino-3-methyloxetane → Rac-5-[3-(4-fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-2-methyl-2h-pyrazole-3-carboxylic acid (3-methyl-oxetan-3-yl)-amide

HRID 1695438Notes

Reaction equation

HRID 1695438 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:16]=[C:17]([C:21](O)=[O:22])[N:18]([CH3:20])[N:19]=3)=[C:11]([CH2:24][OH:25])[O:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:26][C:27]1([NH2:31])[CH2:30][O:29][CH2:28]1>>[CH3:26][C:27]1([NH:31][C:21]([C:17]2[N:18]([CH3:20])[N:19]=[C:15]([O:14][CH2:13][C:12]3[C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[N:9][O:10][C:11]=3[CH2:24][OH:25])[CH:16]=2)=[O:22])[CH2:30][O:29][CH2:28]1

Participants

3

Reactant 2

HCID 468357253-Amino-3-methyloxetaneHCID 666438625-[3-(4-fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid

Product 1

HCID 59568412Rac-5-[3-(4-fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-2-methyl-2h-pyrazole-3-carboxylic acid (3-methyl-oxetan-3-yl)-amideYield 50%

Procedure

As described for example 97, 5-[3-(4-fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid (100 mg, 0.29 mmol) was converted, using 3-methyl-3-oxetanamine instead of rac-3-aminotetrahydrofuran, to the title compound (60 mg, 50%) which was obtained as a white foam. MS: m/e=415.1 [M−H]−.

Sources & evidence

ORD record
ord-346b6759d1fe4103b6d7669c41b8582d
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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