Hydrochloric Acid → Ethyl 3-[(4-fluorobenzoyl)amino]-6,6-dimethyl-5,6-dihydropyrrolo[3,4-c]pyrazole-1(4H)-carboxylate hydrochloride

HRID 1626281Notes

Reaction equation

HRID 1626281 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([NH:8][C:9]2[C:10]3[CH2:21][N:20](C(OC(C)(C)C)=O)[C:19]([CH3:30])([CH3:29])[C:11]=3[N:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:13]=2)=[O:7])=[CH:4][CH:3]=1.[ClH:33]>O1CCOCC1>[ClH:33].[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2[C:10]3[CH2:21][NH:20][C:19]([CH3:29])([CH3:30])[C:11]=3[N:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:13]=2)=[O:7])=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11859042HCID 11859042, compound

Product 1

HCID 68649268Ethyl 3-[(4-fluorobenzoyl)amino]-6,6-dimethyl-5,6-dihydropyrrolo[3,4-c]pyrazole-1(4H)-carboxylate hydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

5-tert-Butyl 1-ethyl 3-[(4-fluorobenzoyl)amino]-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate (2.5 g, 5.59 mmol) was dissolved in dioxane (50 ml) and treated with HCl 4M in dioxane (28 ml, 20 eq). After 2 hours at 40° C. (TLC: CH2Cl2/MeOH 90/10) the reaction mixture was concentrated and the residue was treated with diethyl ether, filtered to afford the title compound (2.09 g) as a solid in 98% yield.

Workup

  1. concentrationAfter 2 hours at 40° C. (TLC: CH2Cl2/MeOH 90/10) the reaction mixture was concentrated
  2. additionthe residue was treated with diethyl ether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-fb3cd894deb241b487dee5e5ae7cd80b
Source dataset
uspto-grants-2014_07
Patent number
US08785448B2

Reaction notes

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