tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate → HCID 86707520, compound

HRID 339024Notes

Reaction equation

HRID 339024 reaction equation
[F:1][C:2]([F:26])([F:25])[C@H:3]([N:12]1[CH2:16][CH2:15][C@H:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13]1)[C:4]1[CH:5]=[N:6][C:7]([NH:10][NH2:11])=[CH:8][CH:9]=1.[Br:27][C:28]1[C:37]([CH3:38])=[C:36]2[C:31]([CH:32]=[CH:33][C:34]([CH:39]=O)=[N:35]2)=[CH:30][CH:29]=1>>[Br:27][C:28]1[C:37]([CH3:38])=[C:36]2[C:31]([CH:32]=[CH:33][C:34]([C:39]3[N:6]4[CH:5]=[C:4]([C@@H:3]([N:12]5[CH2:16][CH2:15][C@H:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:23])[CH3:21])[CH2:13]5)[C:2]([F:25])([F:1])[F:26])[CH:9]=[CH:8][C:7]4=[N:10][N:11]=3)=[N:35]2)=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 86707414tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamateHCID 86707521HCID 86707521, compound

Product 1

HCID 86707520HCID 86707520, compoundYield 79%

Procedure

Prepared as described in Example 9B, Step F, using tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (0.80 g, 2.13 mmol) and 7-bromo-8-methylquinoline-2-carbaldehyde (0.533 g, 2.13 mmol) in place of 8-methoxyquinoline-2-carbaldehyde to provide tert-butyl (S)-1-((R)-1-(3-(7-bromo-8-methylquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-ylcarbamate (1.01 g, 79%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-917d8890a45b498e87c86712b75cdf0b
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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