[3-[3-(Dimethylamino)-1-oxo-2-propenyl]phenyl]methylcarbamic acid, methyl ester → [3-[3-(2-Furanylcarbonyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]methylcarbamic acid, methyl ester

HRID 1906849Notes

Reaction equation

HRID 1906849 reaction equation
C[N:2]([CH3:19])[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[C:9]([CH2:13][NH:14][C:15](=[O:18])[O:16][CH3:17])[CH:10]=[CH:11][CH:12]=1)=O.NC1[C:25]([C:26]([C:28]2[O:29][CH:30]=[CH:31][CH:32]=2)=[O:27])=[CH:24][NH:23][N:22]=1>C(O)(=O)C>[O:29]1[CH:30]=[CH:31][CH:32]=[C:28]1[C:26]([C:25]1[CH:24]=[N:23][N:22]2[C:5]([C:7]3[CH:8]=[C:9]([CH2:13][NH:14][C:15](=[O:18])[O:16][CH3:17])[CH:10]=[CH:11][CH:12]=3)=[CH:4][CH:3]=[N:2][C:19]=12)=[O:27]

Participants

4

Reactant 2

HCID 86741391[3-[3-(Dimethylamino)-1-oxo-2-propenyl]phenyl]methylcarbamic acid, methyl esterHCID 178509268HCID 178509268, compound

Product 1

HCID 86741390[3-[3-(2-Furanylcarbonyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]methylcarbamic acid, methyl esterYield 77.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A reaction mixture comprising 2.62 g of [3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]methylcarbamic acid, methyl ester, 1.77 g of 3-amino-4-furoylpyrazole and 100 ml of glacial acetic acid was reacted as described in Example 29, giving 2.90 g of the desired product, mp 152°-154° C.

Sources & evidence

ORD record
ord-5dea22ac3e784594b4bada15033ec1a4
Source dataset
uspto-grants-1987_03
Patent number
US04654347

Reaction notes

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