Hydrochloric Acid → HCID 68983780, compound

HRID 1472212Notes

Reaction equation

[CH2:1]([O:3][C:4]([N:6]1[C:10]([NH:11][C:12](=[O:29])[C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[CH:15][C:14]=2[N+:26]([O-])=O)=[C:9]2[CH2:30][N:31]([S:35]([C:38]3[CH:43]=[C:42]([F:44])[CH:41]=[C:40]([F:45])[CH:39]=3)(=[O:37])=[O:36])[C:32]([CH3:34])([CH3:33])[C:8]2=[N:7]1)=[O:5])[CH3:2].C1CCCCC=1.[ClH:52]>O1CCCC1.O.C(O)C.[Pd]>[ClH:52].[ClH:52].[CH2:1]([O:3][C:4]([N:6]1[C:10]([NH:11][C:12](=[O:29])[C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[CH:15][C:14]=2[NH2:26])=[C:9]2[CH2:30][N:31]([S:35]([C:38]3[CH:43]=[C:42]([F:44])[CH:41]=[C:40]([F:45])[CH:39]=3)(=[O:37])=[O:36])[C:32]([CH3:34])([CH3:33])[C:8]2=[N:7]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of 5-(3,5-difluoro-benzenesulfonyl)-6,6-dimethyl-3-[4-(4-methyl-piperazin-1 yl)-2-nitro-benzoylamino]-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-2-carboxylic acid ethyl ester (1.50 g, 2.3 mmol), cyclohexene (15 eq., 20 mL), 2N HCl (13 eq., 15 mL), in tetrahydrofuran-water-ethanol (2:1.5:1.5, 50 mL) was treated with 10% Pd—C (0.55 g). The reaction mixture was stirred at 70° C. for 3 hours, and then filtered on decalite. The filtering pad was washed thoroughly with tetrahydrofuran and ethanol. The filtrate was then evaporated to dryness affording the title compound as beige powder (1.4 g, 93% yield) that was used in the next steps without any further purification.

Workup

filtrationfiltered on decalite
washThe filtering pad was washed thoroughly with tetrahydrofuran and ethanol
customThe filtrate was then evaporated to dryness

Sources & evidence

ORD record: ord-e0d03d2989094297a132e6bc300ea8b3
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012487B2

Reaction notes

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