Carbamate → tert-butyl 2-fluoroethyl((S)-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-yl)carbamate

HRID 338880Notes

Reaction equation

HRID 338880 reaction equation
[F:1][CH2:2][CH2:3][N:4]([C@H:12]1[CH2:16][CH2:15][N:14]([C@H:17]([C:22]2[CH:23]=[N:24][C:25]([NH:28][NH2:29])=[CH:26][CH:27]=2)[C:18]([F:21])([F:20])[F:19])[CH2:13]1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(=O)([O-])N.[CH:34]([O:37][C:38]1[CH:39]=[CH:40][CH:41]=[C:42]2[C:47]=1[N:46]=[C:45]([CH:48]=O)[CH:44]=[CH:43]2)([CH3:36])[CH3:35]>>[F:1][CH2:2][CH2:3][N:4]([C@H:12]1[CH2:16][CH2:15][N:14]([C@H:17]([C:22]2[CH:27]=[CH:26][C:25]3[N:24]([C:48]([C:45]4[CH:44]=[CH:43][C:42]5[C:47](=[C:38]([O:37][CH:34]([CH3:36])[CH3:35])[CH:39]=[CH:40][CH:41]=5)[N:46]=4)=[N:29][N:28]=3)[CH:23]=2)[C:18]([F:21])([F:19])[F:20])[CH2:13]1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 3

HCID 276CarbamateHCID 822418228-Isopropoxyquinoline-2-carbaldehydeHCID 86707428tert-butyl 2-fluoroethyl((S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-yl)carbamate

Product 1

HCID 86707429tert-butyl 2-fluoroethyl((S)-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-yl)carbamate

Procedure

Prepared as described in Example 9B, Step F, using tert-butyl 2-fluoroethyl((S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-yl)carbamate (0.10 g, 0.237 mmol) in place of tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-yl)carbamate and using 8-isopropoxyquinoline-2-carbaldehyde (0.051 g, 0.237 mmol) in place of 8-methoxyquinoline-2-carbaldehyde. LCMS APCI (+) m/z 617 (M+H).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-30ade4b590954bc2a0536e4ca41c1426
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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