(R)-3-Pyrrolidinol → 6-[8-((R)-3-hydroxy-pyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamino]-3,3-dimethyl-1,3-dihydro-indol-2-one

HRID 2273015Notes

Reaction equation

HRID 2273015 reaction equation
[NH2:1][C:2]1[N:16]=[C:5]2[C:6]([N:10]3[CH2:14][CH2:13][C@@H:12]([OH:15])[CH2:11]3)=[N:7][CH:8]=[CH:9][N:4]2[N:3]=1.ClC1C2N(N=C(N)N=2)C=CN=1.N1CC[C@@H](O)C1.Cl[C:35]1[CH:43]=[C:42]2[C:38]([C:39]([CH3:46])([CH3:45])[C:40](=[O:44])[NH:41]2)=[CH:37][CH:36]=1>>[OH:15][C@@H:12]1[CH2:13][CH2:14][N:10]([C:6]2[C:5]3[N:4]([N:3]=[C:2]([NH:1][C:35]4[CH:43]=[C:42]5[C:38]([C:39]([CH3:46])([CH3:45])[C:40](=[O:44])[NH:41]5)=[CH:37][CH:36]=4)[N:16]=3)[CH:9]=[CH:8][N:7]=2)[CH2:11]1

Participants

5

Reactant 4

HCID 2759337(R)-3-PyrrolidinolHCID 583989576-chloro-3,3-dimethyl-2,3-dihydro-1H-indol-2-oneHCID 772310108-Chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-amineHCID 89767228(R)-1-(2-Amino-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-pyrrolidin-3-ol

Product 1

HCID 897672836-[8-((R)-3-hydroxy-pyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamino]-3,3-dimethyl-1,3-dihydro-indol-2-one

Procedure

(R)-1-(2-Amino-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-pyrrolidin-3-ol, synthesized by reaction of 8-chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine and (R)-pyrrolidin-3-ol following general procedure 3, is coupled with 6-chloro-3,3-dimethyl-1,3-dihydro-indol-2-one under Buchwald Hartwig conditions using general procedure 2.

Sources & evidence

ORD record
ord-1c78da2f5b5b4a458f829131bd007fba
Source dataset
uspto-grants-2015_09
Patent number
US09120804B2

Reaction notes

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