8-Methoxyquinoline-2-carbaldehyde → tert-butyl 3-(fluoromethyl)-1-((R)-2,2,2-trifluoro-1-(3-(8-methoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate

HRID 338996Notes

Reaction equation

HRID 338996 reaction equation
[F:1][CH2:2][C:3]1([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:7][CH2:6][N:5]([C@H:8]([C:13]2[CH:14]=[N:15][C:16]([NH:19][NH2:20])=[CH:17][CH:18]=2)[C:9]([F:12])([F:11])[F:10])[CH2:4]1.[CH3:29][O:30][C:31]1[CH:32]=[CH:33][CH:34]=[C:35]2[C:40]=1[N:39]=[C:38]([CH:41]=O)[CH:37]=[CH:36]2>>[F:1][CH2:2][C:3]1([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:27])[CH3:26])[CH2:7][CH2:6][N:5]([C@H:8]([C:13]2[CH:18]=[CH:17][C:16]3[N:15]([C:41]([C:38]4[CH:37]=[CH:36][C:35]5[C:40](=[C:31]([O:30][CH3:29])[CH:32]=[CH:33][CH:34]=5)[N:39]=4)=[N:20][N:19]=3)[CH:14]=2)[C:9]([F:12])([F:10])[F:11])[CH2:4]1

Participants

3

Reactant 2

HCID 15488708-Methoxyquinoline-2-carbaldehydeHCID 86707490tert-butyl 3-(fluoromethyl)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate

Product 1

HCID 86707505tert-butyl 3-(fluoromethyl)-1-((R)-2,2,2-trifluoro-1-(3-(8-methoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate

Procedure

Prepared as described in Example 9B using tert-butyl 3-(fluoromethyl)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (Example 154; 0.20 g, 0.491 mmol) in place of tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidine-3-ylcarbamate and 8-methoxyquinoline-2-carbaldehyde (0.092 g, 0.491 mmol) in Step E (0.229 g, 81%). LCMS APCI (+) m/z 575 (M+H).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-06fd6a9ab1814d35b507cfc9c4bc67a8
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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