Cyclohexene → HCID 86643845, compound

HRID 1640993Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([S:9]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:16]=[C:15]3[NH:40][C:41](=[O:64])[C:42]2[CH:47]=[CH:46][C:45]([N+:48]([O-])=O)=[CH:44][C:43]=2[N:51]([CH:58]2[CH2:63][CH2:62][O:61][CH2:60][CH2:59]2)[C:52](=[O:57])[C:53]([F:56])([F:55])[F:54])(=[O:11])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1.C1CCCCC=1>O1CCOCC1.[Pd]>[NH2:48][C:45]1[CH:46]=[CH:47][C:42]([C:41]([NH:40][C:15]2[C:14]3[C:18](=[CH:19][CH:20]=[C:12]([S:9]([C:4]4[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=4)(=[O:10])=[O:11])[CH:13]=3)[N:17]([C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:16]=2)=[O:64])=[C:43]([N:51]([CH:58]2[CH2:59][CH2:60][O:61][CH2:62][CH2:63]2)[C:52](=[O:57])[C:53]([F:56])([F:54])[F:55])[CH:44]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of N-[5-(3,5-difluoro-benzenesulfonyl)-1-trityl-1H-indazol-3-yl]-4-nitro-2-[(tetrahydro-pyran-4-yl)-(2,2,2-trifluoro-acetyl)-amino]-benzamide (4.05 g, 4.5 mmol) in 1,4-dioxane (100 mL) was added cyclohexene (10 mL) and 10% Pd/C (405 mg). The mixture was stirred at 90° C. for 5 hours, filtered and evaporated to dryness. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate/n-hexane 2:1 affording the title compound as white solid (2.9 g).

Workup

filtrationfiltered
customevaporated to dryness
customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate/n-hexane 2:1 affording the title compound as white solid (2.9 g)

Sources & evidence

ORD record: ord-45f0aea8d2f541899284056fbbbc9467
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114865B2

Reaction notes

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