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

HRID 1753017Notes

Reaction equation

HRID 1753017 reaction equation
[NH2:1][C:2]1[CH:3]=[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:5]=[N:6][CH:7]=1.[F:31][C:32]([F:44])([F:43])[C:33]1[CH:34]=[C:35]([CH2:39][C:40](O)=[O:41])[CH:36]=[CH:37][CH:38]=1.CCN(C(C)C)C(C)C>>[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:41])[CH2:39][C:35]3[CH:36]=[CH:37][CH:38]=[C:33]([C:32]([F:43])([F:31])[F:44])[CH:34]=3)[CH:7]=[N:6][CH:5]=2)=[O:9])=[CH:11]1)([CH3:29])[CH3:30]

Participants

4

Reactant 3

HCID 676953-(Trifluoromethyl)benzeneacetic acidHCID 81531DiisopropylethylamineHCID 90093072(5-aminopyridin-3-yl)[1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]methanone

Product 1

HCID 118341198N-(5-{[1-(1-hydroxy-2-methylpropan-2-yl)-1H-pyrrolo[3,2-c]pyridin-3-yl]carbonyl}pyridin-3-yl)-2-[3-(trifluoromethyl)phenyl]acetamide

Procedure

Prepared according to Method 1 (Example 19) using (5-aminopyridin-3-yl)[1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]methanone (Preparation 28), 3-trifluoromethylphenylacetic acid and DIPEA. The residue was purified using silica gel column chromatography eluting with 80% 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. customThe residue was purified
  3. washeluting with 80% 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-92584230734d4eb2b2f5a95ed30ca46f
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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