1,1-Dimethoxyethyl(dimethyl)amine → Fasiplon

HRID 256319Notes

Reaction equation

HRID 256319 reaction equation
[CH2:1]([C:3]1[C:4]([O:17][CH3:18])=[N:5][C:6]2[N:7]([CH:10]=[C:11]([C:13]([NH:15][OH:16])=[NH:14])[N:12]=2)[C:8]=1[CH3:9])[CH3:2].CO[C:21](OC)(N(C)C)[CH3:22]>>[CH2:1]([C:3]1[C:4]([O:17][CH3:18])=[N:5][C:6]2[N:7]([CH:10]=[C:11]([C:13]3[N:14]=[C:21]([CH3:22])[O:16][N:15]=3)[N:12]=2)[C:8]=1[CH3:9])[CH3:2]

Participants

3

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 178437279HCID 178437279, compound

Product 1

HCID 208954FasiplonYield 95%

Conditions

Temperature
100 °C

Procedure

A mixture of 1.70 g of 6-ethyl-N-hydroxy-7-methoxy-5-methylimidazo[1,2-a]pyrimidine-2-carboxamidine and 3.5 ml of dimethylacetamide dimethyl acetal was heated at 100° C. for 15 minutes and the resulting mixture was evaporated to dryness and purified by flash chromatography. The resulting solid was crystallized from aqueous methanol to give 1.76 g of 6-ethyl-7-methoxy-5-methyl-2-(5-methyl-1,2,4-oxadiazol-3-yl)imidazol[1,2-a]pyrimidine (95% yield) as a white crystalline solid melting at 176°-177° C.

Workup

  1. customthe resulting mixture was evaporated to dryness
  2. custompurified by flash chromatography
  3. customThe resulting solid was crystallized from aqueous methanol

Sources & evidence

ORD record
ord-0fe4e66ede894bc59cef1b3e140a595d
Source dataset
uspto-grants-1987_10
Patent number
US04703049

Reaction notes

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