3-(Trifluoromethyl)benzeneacetic acid → N-(5-{[7-fluoro-1-(1-hydroxypropan-2-yl)-1H-pyrrolo[3,2-c]pyridin-3-yl]carbonyl}pyridin-3-yl)-2-[3-(trifluoromethyl)phenyl]acetamide

HRID 1753010Notes

Reaction equation

HRID 1753010 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=O)[CH:6]=[CH:7][CH:8]=1.[NH2:15][C:16]1[CH:17]=[C:18]([C:22]([C:24]2[C:28]3[CH:29]=[N:30][CH:31]=[C:32]([F:33])[C:27]=3[N:26]([CH:34]([CH3:37])[CH2:35][OH:36])[CH:25]=2)=[O:23])[CH:19]=[N:20][CH:21]=1>>[F:33][C:32]1[C:27]2[N:26]([CH:34]([CH3:37])[CH2:35][OH:36])[CH:25]=[C:24]([C:22]([C:18]3[CH:17]=[C:16]([NH:15][C:10](=[O:12])[CH2:9][C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:14])[F:13])[CH:4]=4)[CH:21]=[N:20][CH:19]=3)=[O:23])[C:28]=2[CH:29]=[N:30][CH:31]=1

Participants

3

Reactant 2

HCID 676953-(Trifluoromethyl)benzeneacetic acidHCID 90093760HCID 90093760, compound

Product 1

HCID 118341210N-(5-{[7-fluoro-1-(1-hydroxypropan-2-yl)-1H-pyrrolo[3,2-c]pyridin-3-yl]carbonyl}pyridin-3-yl)-2-[3-(trifluoromethyl)phenyl]acetamide

Procedure

Prepared according to Method M (Example 206) using 3-trifluoromethylphenylacetic acid and (5-aminopyridin-3-yl)[7-fluoro-1-(2-hydroxy-1-methylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]methanone (Enantiomer 2, Preparation 26). The residue was purified using preparative TLC eluting with 5% MeOH in EtOAc.

Workup

  1. customPrepared
  2. customThe residue was purified
  3. washeluting with 5% MeOH in EtOAc

Sources & evidence

ORD record
ord-e50f6514c94d4996a0e46b9374b86459
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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