3-(Trifluoromethyl)benzeneacetic acid → N-(2-{[1-(1-hydroxy-2-methylpropan-2-yl)-1H-pyrrolo[3,2-c]pyridin-3-yl]carbonyl}pyridin-4-yl)-2-[3-(trifluoromethyl)phenyl]acetamide

HRID 1753015Notes

Reaction equation

HRID 1753015 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([C:10]2[C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:13]=3[N:12]([C:19]([CH3:30])([CH3:29])[CH2:20][O:21][Si](C(C)(C)C)(C)C)[CH:11]=2)=[O:9])[CH:3]=1.[F:31][C:32]([F:44])([F:43])[C:33]1[CH:34]=[C:35]([CH2:39][C:40]([OH:42])=O)[CH:36]=[CH:37][CH:38]=1>>[OH:21][CH2:20][C:19]([N:12]1[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[C:10]([C:8]([C:4]2[CH:3]=[C:2]([NH:1][C:40](=[O:42])[CH2:39][C:35]3[CH:36]=[CH:37][CH:38]=[C:33]([C:32]([F:31])([F:44])[F:43])[CH:34]=3)[CH:7]=[CH:6][N:5]=2)=[O:9])=[CH:11]1)([CH3:30])[CH3:29]

Participants

3

Reactant 2

HCID 676953-(Trifluoromethyl)benzeneacetic acidHCID 90093653(4-aminopyridin-2-yl)[1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]methanone

Product 1

HCID 118341199N-(2-{[1-(1-hydroxy-2-methylpropan-2-yl)-1H-pyrrolo[3,2-c]pyridin-3-yl]carbonyl}pyridin-4-yl)-2-[3-(trifluoromethyl)phenyl]acetamide

Procedure

Prepared according to Method M (Example 206) using (4-aminopyridin-2-yl)[1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]methanone (Preparation 27) and 3-trifluoromethylphenylacetic acid at 70° C. The residue was purified over neutral alumina eluting with 50%-60% EtOAc in hexane followed by acid deprotection using 10% HCl in dioxane at room temperature for 18 hours. The reaction was concentrated in vacuo and purified using preparative HPLC to afford the title compound.

Workup

  1. customPrepared
  2. customat 70° C
  3. customThe residue was purified over neutral alumina eluting with 50%-60% EtOAc in hexane
  4. customat room temperature
  5. customfor 18 hours
  6. concentrationThe reaction was concentrated in vacuo
  7. custompurified

Sources & evidence

ORD record
ord-a2dc18fb47ed4f82b80012fd61c62f3d
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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