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

HRID 338980Notes

Reaction equation

HRID 338980 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.[CH:29]([O:32][C:33]1[CH:34]=[CH:35][CH:36]=[C:37]2[C:42]=1[N:41]=[C:40]([CH:43]=O)[CH:39]=[CH:38]2)([CH3:31])[CH3:30]>>[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:43]([C:40]4[CH:39]=[CH:38][C:37]5[C:42](=[C:33]([O:32][CH:29]([CH3:31])[CH3:30])[CH:34]=[CH:35][CH:36]=5)[N:41]=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 822418228-Isopropoxyquinoline-2-carbaldehydeHCID 86707490tert-butyl 3-(fluoromethyl)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate

Product 1

HCID 86707489tert-butyl 3-(fluoromethyl)-1-((R)-2,2,2-trifluoro-1-(3-(8-isopropoxyquinolin-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 in place of tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidine-3-ylcarbamate and substituting 8-isopropoxyquinoline-2-carbaldehyde in Step F. LCMS APCI (+) m/z 603 (M+H).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-cd547640e4274848972b49ed2f21d843
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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