HCID 57552218, compound → HCID 57552217, compound

HRID 1986899Notes

Reaction equation

C([N:8]1[C:37]([CH3:38])=[C:11]2[C:12](=[O:36])[N:13]([CH2:24][CH:25]([F:35])[CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:14]3[CH:15]=[C:16]4[CH2:23][CH2:22][CH2:21][CH2:20][C:17]4=[CH:18][C:19]=3[C:10]2=[N:9]1)C1C=CC=CC=1>[Pd].CN(C=O)C.CO>[F:35][CH:25]([CH2:24][N:13]1[C:14]2[CH:15]=[C:16]3[CH2:23][CH2:22][CH2:21][CH2:20][C:17]3=[CH:18][C:19]=2[C:10]2=[N:9][NH:8][C:37]([CH3:38])=[C:11]2[C:12]1=[O:36])[CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:31])([CH3:33])[CH3:32]

Participants

Conditions

Temperature: 23 °C

Procedure

A mixture of tert-butyl 3-(2-benzyl-3-methyl-4-oxo-2,4,7,8,9,10-hexahydro-5H-benzo[g]pyrazolo[4,3-c]quinolin-5-yl)-2-fluoropropylcarbamate (1-10) (0.10 g, 0.19 mmol, 1 equiv) and 10% palladium on carbon (300 mg) in DMF (10 mL) and methanol (10 mL) was stirred under a hydrogen balloon at 23° C. for 72 h. The resulting suspension was filtered and the filtrate was concentrated to yield tert-butyl 2-fluoro-3-(3-methyl-4-oxo-2,4,7,8,9,10-hexahydro-5H-benzo[g]pyrazolo[4,3-c]quinolin-5-yl)propylcarbamate (1-11). LRMS m/z (M+H) 429.2 found, 429.2 required.

Workup

filtrationThe resulting suspension was filtered
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-3d3e884001e14f0a90b889487d6ce75e
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07550477B2

Reaction notes

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