3-Hydroxyazetidine → 6-[8-(3-Hydroxy-azetidin-1-yl)-(1,2,4]triazolo[1,5-a]pyrazin-2-ylamino]-3,3-dimethyl-1,3-dihydro-indol-2-one

HRID 2273016Notes

Reaction equation

HRID 2273016 reaction equation
[NH2:1][C:2]1[N:15]=[C:5]2[C:6]([N:10]3[CH2:13][CH:12]([OH:14])[CH2:11]3)=[N:7][CH:8]=[CH:9][N:4]2[N:3]=1.N1CC(O)C1.Cl[C:22]1[CH:30]=[C:29]2[C:25]([C:26]([CH3:33])([CH3:32])[C:27](=[O:31])[NH:28]2)=[CH:24][CH:23]=1>>[OH:14][CH:12]1[CH2:11][N:10]([C:6]2[C:5]3[N:4]([N:3]=[C:2]([NH:1][C:22]4[CH:30]=[C:29]5[C:25]([C:26]([CH3:33])([CH3:32])[C:27](=[O:31])[NH:28]5)=[CH:24][CH:23]=4)[N:15]=3)[CH:9]=[CH:8][N:7]=2)[CH2:13]1

Participants

4

Reactant 3

HCID 15142903-HydroxyazetidineHCID 583989576-chloro-3,3-dimethyl-2,3-dihydro-1H-indol-2-oneHCID 117818191HCID 117818191, compound

Product 1

HCID 897690486-[8-(3-Hydroxy-azetidin-1-yl)-(1,2,4]triazolo[1,5-a]pyrazin-2-ylamino]-3,3-dimethyl-1,3-dihydro-indol-2-one

Procedure

1-(2-Amino-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-azetidin-3-ol, available by nucleophilic substitution of 8-chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine with azetidin-3-ol using general procedure 3, is reacted under amination conditions described in general procedure 2 with 6-chloro-3,3-dimethyl-1,3-dihydro-indol-2-one giving the title compound as a solid.

Sources & evidence

ORD record
ord-6b295dc8667e4bc99b8ce4ce39dfbf7c
Source dataset
uspto-grants-2015_09
Patent number
US09120804B2

Reaction notes

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