Chloroacetaldehyde → 2-fluoro-4-imidazo[1,2-a]pyrimidin-6-yl-N-methylbenzamide

HRID 1257787Notes

Reaction equation

HRID 1257787 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([NH:14][CH3:15])=[O:13])=[C:10]([F:18])[CH:9]=2)=[CH:4][N:3]=1.Cl[CH2:20][CH:21]=O>C(O)(C)C>[F:18][C:10]1[CH:9]=[C:8]([C:5]2[CH:4]=[N:3][C:2]3[N:7]([CH:20]=[CH:21][N:1]=3)[CH:6]=2)[CH:17]=[CH:16][C:11]=1[C:12]([NH:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 672245484-(2-aminopyrimidin-5-yl)-2-fluoro-N-methylbenzamide

Product 1

HCID 672248512-fluoro-4-imidazo[1,2-a]pyrimidin-6-yl-N-methylbenzamideYield 88.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(2-aminopyrimidin-5-yl)-2-fluoro-N-methylbenzamide (123 mg, 0.5 mmol) and chloroacetaldehyde (0.318 mL, 2.5 mmol) in isopropyl alcohol (4 mL) was stirred at 90° C. for 4 h. The solvent was removed under vacuum and the residue was triturated with ethyl acetate and hexanes. The solid formed was collected and dried under reduced pressure to give the desired product (120 mg, 88.8%). LCMS: (M+H)=271.0.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was triturated with ethyl acetate and hexanes
  3. customThe solid formed
  4. customwas collected
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-69a3636056ac4d6eaf170b9a8cfa885d
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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