Methanol → HCID 86713609, compound

HRID 524093Notes

Reaction equation

HRID 524093 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-29691528144d4ac085aedde3569dbe7a
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Reaction notes

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