Cyclopropanecarbonyl chloride → HCID 86657967, compound

HRID 2366765Notes

Reaction equation

HRID 2366765 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([N:11]([CH3:25])[C:12]1[CH:13]=[C:14]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH:15]=[CH:16][CH:17]=1)[N:5]=2.[CH:26]1([C:29](Cl)=[O:30])[CH2:28][CH2:27]1>N1C=CC=CC=1.C(OCC)(=O)C>[CH3:25][N:11]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH:13]=1)[C:6]1[N:5]=[C:4]2[S:3][C:2]([NH:1][C:29]([CH:26]3[CH2:28][CH2:27]3)=[O:30])=[N:10][C:9]2=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 86657965HCID 86657965, compound

Product 1

HCID 86657967HCID 86657967, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-{3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)(methyl)amino]phenyl}-2,2,2-trifluoroacetamide (174 mg, 0.474 mmol) in pyridine (1.7 mL) was added cyclopropanecarbonyl chloride (55 μL, 0.610 mmol) at −20° C., and the mixture was stirred for 2 hr. The reaction mixture was diluted with ethyl acetate (50 mL), washed with water (20 mL) and saturated brine (20 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=80/20→0/100) to give the title compound (147 mg, 71%) as a pale-violet powder.

Workup

  1. washwashed with water (20 mL) and saturated brine (20 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=80/20→0/100)

Sources & evidence

ORD record
ord-567e14e4561140c1ae8f9dd2f27c2292
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

Loading…