(R)-1-((S)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ol → (R)-1-((S)-2,2,2-trifluoro-1-(3-(8-isopropoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ol

HRID 338900Notes

Reaction equation

HRID 338900 reaction equation
[F:1][C:2]([F:19])([F:18])[C@@H:3]([N:12]1[CH2:16][CH2:15][C@@H:14]([OH:17])[CH2:13]1)[C:4]1[CH:5]=[N:6][C:7]([NH:10][NH2:11])=[CH:8][CH:9]=1.[CH:20]([O:23][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:33]=1[N:32]=[C:31]([CH:34]=O)[CH:30]=[CH:29]2)([CH3:22])[CH3:21]>>[F:19][C:2]([F:1])([F:18])[C@@H:3]([N:12]1[CH2:16][CH2:15][C@@H:14]([OH:17])[CH2:13]1)[C:4]1[CH:9]=[CH:8][C:7]2[N:6]([C:34]([C:31]3[CH:30]=[CH:29][C:28]4[C:33](=[C:24]([O:23][CH:20]([CH3:22])[CH3:21])[CH:25]=[CH:26][CH:27]=4)[N:32]=3)=[N:11][N:10]=2)[CH:5]=1

Participants

3

Reactant 2

HCID 70983872(R)-1-((S)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-olHCID 822418228-Isopropoxyquinoline-2-carbaldehyde

Product 1

HCID 71004918(R)-1-((S)-2,2,2-trifluoro-1-(3-(8-isopropoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ol

Procedure

Prepared as described in Example 9B, Steps A-F, using (R)-1-((S)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ol in place of tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate and using 8-isopropoxyquinoline-2-carbaldehyde in place of 8-methoxyquinoline-2-carbaldehyde in Step F. LCMS APCI (+) m/z 472.1 (M+H).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-bd40b1d66336436dba626524d0b83a1e
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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