Methanol → HCID 86713609, compound

HRID 2404075Notes

Reaction equation

HRID 2404075 reaction equation
[C:1]([C:3]1[C:4]2[N:5]([C:9]([C:12]3[CH:13]=[C:14]([NH:22][C:23]([NH:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[O:24])[CH:15]=[C:16]([O:18][CH:19]([CH3:21])[CH3:20])[CH:17]=3)=[CH:10][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].CO>N.[Pd]>[NH2:2][CH2:1][C:3]1[C:4]2[N:5]([C:9]([C:12]3[CH:13]=[C:14]([NH:22][C:23]([NH:25][CH2:26][C:27]([F:29])([F:30])[F:28])=[O:24])[CH:15]=[C:16]([O:18][CH:19]([CH3:21])[CH3:20])[CH:17]=3)=[CH:10][N:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 86713608HCID 86713608, compound

Product 1

HCID 86713609HCID 86713609, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 222AmmoniaSolvent

Procedure

1-(3-(8-cyanoimidazo[1,2-a]pyridin-3-yl)-5-isopropoxyphenyl)-3-(2,2,2-trifluoroethyl)urea (0.030 g, 0.072 mmol) was taken up in 7N AMMONIA in methanol (20 mL, 140 mmol) and Pd—C (10 mg, 0.094 mmol) added. Reaction was stirred under H2 balloon for 1 hour. Mixture was then filtered through celite and solvent removed. Residue was dried under high vacuum overnight to to give title compound as a yellow solid (0.026 g, 0.062 mmol, 86% yield). MS (ES+) C20H22F3N5O2 requires: 421. found: 422 [M+H]+.

Workup

  1. customReaction
  2. filtrationMixture was then filtered through celite and solvent
  3. customremoved
  4. customResidue was dried under high vacuum overnight

Sources & evidence

ORD record
ord-0cf8c408ea8343d7b33e108ff52046ba
Source dataset
uspto-grants-2014_08
Patent number
US08802697B2

Reaction notes

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