Azetidine → HCID 67968033, compound

HRID 1802307Notes

Reaction equation

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

Participants

Reactant 2

HCID 10422Azetidine

HCID 67774177HCID 67774177, compound

Product 1

HCID 67968033HCID 67968033, compoundYield 83.7%

Procedure

The product was prepared in the same manner as described in example 70f using 5-(2-(cyclopropyl(methyl)amino)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid (70 mg, 197 μmol) and azetidine (52.9 μl, 788 μmol) as starting materials. The reaction affords 4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid [2-(cyclopropyl-methyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-amide (65 mg, 83.7%) as off-white solid. mp: 229.6, MS: m/z=395.0 (M+H+).

Workup

customThe product was prepared in the same manner

Sources & evidence

ORD record: ord-594b1f045cda4e96aade56f5a8f659c6
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349824B2

Reaction notes

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