(5-chloro-2-fluorophenyl)hydrazine → (s)-Tert-butyl 2-(1-(5-chloro-2-fluorophenyl)-1,4,6,7-tetrahydropyrano[4,3-c]pyrazole-3-carboxamido)-3,3-dimethylbutanoate

HRID 242507Notes

Reaction equation

HRID 242507 reaction equation
FC1C=C(N2[C:13]3[CH2:14][CH2:15][O:16][CH2:17][C:12]=3[C:11]([C:18](N[C@@H](C(C)(C)C)C(NC)=O)=[O:19])=N2)C=CC=1F.[F:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=1[NH:38][NH2:39].[C:40]([O:44][C:45](=[O:52])[C@H:46]([C:48]([CH3:51])([CH3:50])[CH3:49])[NH2:47])([CH3:43])([CH3:42])[CH3:41]>>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([F:30])=[C:32]([N:38]2[C:13]3[CH2:14][CH2:15][O:16][CH2:17][C:12]=3[C:11]([C:18]([NH:47][C@@H:46]([C:48]([CH3:51])([CH3:50])[CH3:49])[C:45]([O:44][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:52])=[O:19])=[N:39]2)[CH:33]=1

Participants

4

Reactant 3

HCID 2773732(5-chloro-2-fluorophenyl)hydrazineHCID 11252445L-(+)-Ttert-butyl tert-leuc-inateHCID 46863093(s)-1-(3,4-Difluorophenyl)-n-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-1,4,6,7-tetrahydropyrano[4,3-c]pyrazole-3-carboxamide

Product 1

HCID 58504324(s)-Tert-butyl 2-(1-(5-chloro-2-fluorophenyl)-1,4,6,7-tetrahydropyrano[4,3-c]pyrazole-3-carboxamido)-3,3-dimethylbutanoate

Procedure

This intermediate was prepared according to the procedure escribed for the synthesis of Compound 114 by replacing 3,4-difluorophenylhydrazine with 2-fluoro-5-chlorophenylhydrazine in step 1, and replacing tert-leucine methyl amide with tert-leucine tert-butyl ester in step 3. LC-MS (+ESI) m/z=466.3 [M+H]+.

Workup

  1. customThis intermediate was prepared

Sources & evidence

ORD record
ord-3ddf0fdf79b141499b63c77621bd3c0e
Source dataset
uspto-grants-2014_02
Patent number
US08653127B2

Reaction notes

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