Cyclohexene → HCID 66735970, compound

HRID 1640987Notes

Reaction equation

HRID 1640987 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:58])[C:42]2[CH:47]=[CH:46][C:45]([N:48]([CH2:50][CH2:51][N:52]([CH3:54])[CH3:53])[CH3:49])=[CH:44][C:43]=2[N+:55]([O-])=O)(=[O:11])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1.C1CCCCC=1>[Pd].O1CCOCC1>[NH2:55][C:43]1[CH:44]=[C:45]([N:48]([CH2:50][CH2:51][N:52]([CH3:54])[CH3:53])[CH3:49])[CH:46]=[CH:47][C:42]=1[C:41]([NH:40][C:15]1[C:14]2[C:18](=[CH:19][CH:20]=[C:12]([S:9]([C:4]3[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=3)(=[O:11])=[O:10])[CH:13]=2)[N:17]([C:21]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=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]=1)=[O:58]

Participants

5

Reactant 2

HCID 8079Cyclohexene2×HCID 66736564HCID 66736564, compound

Product 1

HCID 66735970HCID 66735970, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of N-[5-(3,5-difluoro-benzenesulfonyl)-1-trityl-1H-indazol-3-yl]-4-[(2-dimethylamino-ethyl)-methyl-amino]-2-nitro-benzamide (1.0 g, 1.25 mmol), cyclohexene (2 mL), 1,4-dioxane (50 mL) and 10% Pd/C (0.1 g) was stirred at 85° C. for 5 hours. More cyclohexene (3 mL) and 10% Pd/C (0.2 g) were then added and the mixture stirred at 90° C. for additional 6 hours. The reaction mixture was then cooled to room temperature and filtered over celite washing thoroughly with ethanol. The filtrate was evaporated to dryness affording the title compound as a pale brown solid (910 mg, 94% yield).

Workup

  1. stirringthe mixture stirred at 90° C. for additional 6 hours
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. filtrationfiltered
  4. washover celite washing thoroughly with ethanol
  5. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-efbbd95d92f44c57a95dced759a02e87
Source dataset
uspto-grants-2012_02
Patent number
US08114865B2

Reaction notes

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