Pivaloyl chloride → Ethyl 5-(2,2-dimethylpropanoyl)-3-[(4-fluorobenzoyl)amino]-6,6-dimethyl-5,6-dihydropyrrolo[3,4-c]pyrazole-1(4H)-carboxylate

HRID 448265Notes

Reaction equation

HRID 448265 reaction equation
Cl.[F:2][C:3]1[CH:26]=[CH:25][C:6]([C:7]([NH:9][C:10]2[C:11]3[CH2:22][NH:21][C:20]([CH3:24])([CH3:23])[C:12]=3[N:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:14]=2)=[O:8])=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.[C:36](Cl)(=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38].CCOC(C)=O.CCCCCC>ClCCl>[CH3:38][C:37]([CH3:40])([CH3:39])[C:36]([N:21]1[CH2:22][C:11]2[C:10]([NH:9][C:7](=[O:8])[C:6]3[CH:5]=[CH:4][C:3]([F:2])=[CH:26][CH:25]=3)=[N:14][N:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:12]=2[C:20]1([CH3:23])[CH3:24])=[O:41]

Participants

6

Reactant 4

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 21226206Ethyl acetate hexaneHCID 68649268Ethyl 3-[(4-fluorobenzoyl)amino]-6,6-dimethyl-5,6-dihydropyrrolo[3,4-c]pyrazole-1(4H)-carboxylate hydrochloride

Product 1

HCID 68649346Ethyl 5-(2,2-dimethylpropanoyl)-3-[(4-fluorobenzoyl)amino]-6,6-dimethyl-5,6-dihydropyrrolo[3,4-c]pyrazole-1(4H)-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 3-[(4-fluorobenzoyl)amino]-6,6-dimethyl-5,6-dihydropyrrolo[3,4-c]pyrazole-1(4H)-carboxylate hydrochloride (2.0 g, 5.77 mmol) in dichloromethane (70 ml) was treated, at 0° C., with N,N-diisopropylethylamine (1.6 ml, 9.2 mmol, 1.6 eq) and with pivaloyl chloride (780 μL, 6.3 mmol, 1.1 eq). Gradually, the reaction was brought to room temperature and stirred overnight (TLC: CH2Cl2/EtOAc 90/10). The solution was washed with saturated sodium hydrogencarbonate aqueous solution and brine. The organic phase was dried over sodium sulfate, evaporated and purified by flash chromatography (eluent: CH2Cl2/EtOAc 90/10) to afford 2.03 g of the title compound in 82% yield.

Workup

  1. customwas brought to room temperature
  2. washThe solution was washed with saturated sodium hydrogencarbonate aqueous solution and brine
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated
  5. custompurified by flash chromatography (eluent: CH2Cl2/EtOAc 90/10)

Sources & evidence

ORD record
ord-0386d0c5eba64065b7938631c1296ece
Source dataset
uspto-grants-2013_07
Patent number
US08481585B2

Reaction notes

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