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

HRID 1753013Notes

Reaction equation

HRID 1753013 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]([CH:19]([CH3:29])[CH2:20][O:21][Si](C(C)(C)C)(C)C)[CH:11]=2)=[O:9])[CH:3]=1.[F:30][C:31]([F:43])([F:42])[C:32]1[CH:33]=[C:34]([CH2:38][C:39](O)=[O:40])[CH:35]=[CH:36][CH:37]=1>>[OH:21][CH2:20][CH: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:39](=[O:40])[CH2:38][C:34]3[CH:35]=[CH:36][CH:37]=[C:32]([C:31]([F:42])([F:30])[F:43])[CH:33]=3)[CH:7]=[CH:6][N:5]=2)=[O:9])=[CH:11]1)[CH3:29]

Participants

3

Reactant 2

HCID 676953-(Trifluoromethyl)benzeneacetic acidHCID 90092938(4-aminopyridin-2-yl)[1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]methanone

Product 1

HCID 118341205N-(2-{[1-(1-hydroxypropan-2-yl)-1H-pyrrolo[3,2-c]pyridin-3-yl]carbonyl}pyridin-4-yl)-2-[3-(trifluoromethyl)phenyl]acetamide

Procedure

Prepared according to method described for Method 1 (Example 19) using (4-aminopyridin-2-yl)[1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]methanone (Enantiomer 1, Preparation 30) and 3-trifluoromethylphenylacetic acid. The residue was partitioned between EtOAc and saturated aqueous NaHCO3 solution, the organic layer collected, washed with brine, dried over sodium sulphate and concentrated in vacuo. The residue was dissolved in THF and 10% HCl in dioxane was added. The reaction was stirred 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 partitioned between EtOAc and saturated aqueous NaHCO3 solution
  3. customthe organic layer collected
  4. washwashed with brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in THF
  8. addition10% HCl in dioxane was added
  9. concentrationThe reaction was concentrated in vacuo
  10. custompurified

Sources & evidence

ORD record
ord-519189308c9242a39b36a5f6bbf7e740
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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