3-Ethoxyacryloyl chloride → HCID 136052910, compound

HRID 1977632Notes

Reaction equation

HRID 1977632 reaction equation
[CH2:1]([O:3]/[CH:4]=[CH:5]/[C:6](Cl)=[O:7])[CH3:2].[NH2:9][C:10]1[CH:30]=[CH:29][C:13]([CH2:14][C:15]2[NH:16][C:17](=[O:28])[C:18]3[N:23]([CH3:24])[N:22]=[C:21]([CH2:25][CH2:26][CH3:27])[C:19]=3[N:20]=2)=[CH:12][CH:11]=1>N1C=CC=CC=1>[CH3:24][N:23]1[C:18]2[C:17](=[O:28])[NH:16][C:15]([CH2:14][C:13]3[CH:29]=[CH:30][C:10]([NH:9][C:6](=[O:7])/[CH:5]=[CH:4]/[O:3][CH2:1][CH3:2])=[CH:11][CH:12]=3)=[N:20][C:19]=2[C:21]([CH2:25][CH2:26][CH3:27])=[N:22]1

Participants

4

Reactant 2

HCID 53255003-Ethoxyacryloyl chlorideHCID 1358152625-[(4-Aminophenyl)methyl]-1-methyl-3-propyl-1,4-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Product 1

HCID 136052910HCID 136052910, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(E)-3-ethoxyacryloyl chloride (J. Chem. Soc; 1958,153) (298 mg, 0.0022 mol), was added dropwise to an ice-cooled solution of 5-(4-aminobenzyl)-1-methyl-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-7-one (600 mg, 0.002 mol) in pyridine (15 ml) and the reaction stirred at room temperature for 20 hours. The mixture was partitioned between water (30 ml) and dichloromethane (30 ml), the aqueous layer acidified to pH1 with 2M aqueous hydrochloric acid solution and then extracted with dichloromethane (2×40 ml). The combined organic extracts were dried (MgSO4), filtered and evaporated under reduced pressure, to give, after recrystallisation from ethyl acetate/methanol the title compound (483 mg), m.p.241-243° C.

Workup

  1. customThe mixture was partitioned between water (30 ml) and dichloromethane (30 ml)
  2. extractionextracted with dichloromethane (2×40 ml)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give
  7. customafter recrystallisation from ethyl acetate/methanol the title compound (483 mg), m.p.241-243° C.

Sources & evidence

ORD record
ord-920344beb9654c0b8b85369e03ce3b9a
Source dataset
uspto-grants-2001_05
Patent number
US06235742B1

Reaction notes

Loading…