3,3-Difluoroazetidine hydrochloride → 5-(3,3-Difluoro-azetidin-1-yl)-6-(3-methyl-oxetan-3-ylmethoxy)-pyridine-2-carboxylic acid (1-methyl-1-thiazol-2-yl-ethyl)-amide

HRID 632353Notes

Reaction equation

HRID 632353 reaction equation
[CH3:1][C:2]([NH:9][C:10]([C:12]1[CH:17]=[CH:16][C:15](Br)=[C:14]([O:19][CH2:20][C:21]2([CH3:25])[CH2:24][O:23][CH2:22]2)[N:13]=1)=[O:11])([C:4]1[S:5][CH:6]=[CH:7][N:8]=1)[CH3:3].Cl.[F:27][C:28]1([F:32])[CH2:31][NH:30][CH2:29]1>>[CH3:1][C:2]([NH:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([N:30]2[CH2:31][C:28]([F:32])([F:27])[CH2:29]2)=[C:14]([O:19][CH2:20][C:21]2([CH3:25])[CH2:24][O:23][CH2:22]2)[N:13]=1)=[O:11])([C:4]1[S:5][CH:6]=[CH:7][N:8]=1)[CH3:3]

Participants

3

Reactant 2

HCID 27582473,3-Difluoroazetidine hydrochlorideHCID 710935485-Bromo-6-(3-methyl-oxetan-3-ylmethoxy)-pyridine-2-carboxylic acid (1-methyl-1-thiazol-2-yl-ethyl)-amide

Product 1

HCID 710935325-(3,3-Difluoro-azetidin-1-yl)-6-(3-methyl-oxetan-3-ylmethoxy)-pyridine-2-carboxylic acid (1-methyl-1-thiazol-2-yl-ethyl)-amide

Procedure

The title compound was synthesized in analogy to Example 288b, using 5-bromo-6-(3-methyl-oxetan-3-ylmethoxy)-pyridine-2-carboxylic acid (1-methyl-1-thiazol-2-yl-ethyl)-amide (Example 281c) and 3,3-difluoroazetidine hydrochloride as starting materials, MS (EI): m/e=439.3 [M+H]+.

Sources & evidence

ORD record
ord-071496ac26eb4503a15e325a1cc75eb9
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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