Hydrazine hydrate (1:1) → 2-aminomethyl-N-[5-(3,5-difluoro-benzenesulfonyl)-6,6-dimethyl-1,4,5,6-tetrahydro-pyrrolo[3,4-c]pyrazol-3-yl]-benzamide

HRID 1256641Notes

Reaction equation

HRID 1256641 reaction equation
C(OC([N:6]1[C:10]([NH:11][C:12](=[O:31])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:19][N:20]2C(=O)C3C(=CC=CC=3)C2=O)=[C:9]2[CH2:32][N:33]([S:37]([C:40]3[CH:45]=[C:44]([F:46])[CH:43]=[C:42]([F:47])[CH:41]=3)(=[O:39])=[O:38])[C:34]([CH3:36])([CH3:35])[C:8]2=[N:7]1)=O)C.O.NN>CO.ClCCl>[NH2:20][CH2:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:12]([NH:11][C:10]1[C:9]2[CH2:32][N:33]([S:37]([C:40]3[CH:45]=[C:44]([F:46])[CH:43]=[C:42]([F:47])[CH:41]=3)(=[O:39])=[O:38])[C:34]([CH3:36])([CH3:35])[C:8]=2[NH:7][N:6]=1)=[O:31]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 670087475-(3,5-difluoro-benzenesulfonyl)-3-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-benzoylamino]-6,6-dimethyl-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-2-carboxylic acid ethyl ester

Product 1

HCID 670087052-aminomethyl-N-[5-(3,5-difluoro-benzenesulfonyl)-6,6-dimethyl-1,4,5,6-tetrahydro-pyrrolo[3,4-c]pyrazol-3-yl]-benzamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-(3,5-difluoro-benzenesulfonyl)-3-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-benzoylamino]-6,6-dimethyl-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-2-carboxylic acid ethyl ester (0.23 g, 0.34 mmol) in methanol (15 mL) and dichloromethane (1.5 mL) was added hydrazine hydrate (50 microL, 1.02 mmol). After stirring at reflux for 1 hour the volatiles were removed under reduced pressure and the residue purified by flash chromatography on silica gel eluting with dichloromethane/methanol/7N NH3 in methanol 95:4:1 affording the title compound as colorless oil (93 mg).

Workup

  1. temperatureat reflux for 1 hour the volatiles
  2. customwere removed under reduced pressure
  3. customthe residue purified by flash chromatography on silica gel eluting with dichloromethane/methanol/7N NH3 in methanol 95:4:1 affording the title compound as colorless oil (93 mg)

Sources & evidence

ORD record
ord-e829a30be8c748dca2494ca4068d61e2
Source dataset
uspto-grants-2013_06
Patent number
US08461193B2

Reaction notes

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