HCID 67243837, compound → HCID 25026779, compound

HRID 2422400Notes

Reaction equation

HRID 2422400 reaction equation
C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[F:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19]1[C:24]3([CH2:32][CH2:31][C:30]([CH2:43][C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)([NH:33]CC4C=CC(OC)=CC=4)[CH2:29][CH2:28]3)[O:25][CH2:26][CH2:27][C:18]2=1>O1CCCC1.CO.[Pd]>[CH2:43]([C:30]1([NH2:33])[CH2:31][CH2:32][C:24]2([C:19]3[NH:20][C:21]4[C:17]([C:18]=3[CH2:27][CH2:26][O:25]2)=[CH:16][C:15]([F:14])=[CH:23][CH:22]=4)[CH2:28][CH2:29]1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

5

Reactant 1

HCID 67243837HCID 67243837, compound

Product 1

HCID 25026779HCID 25026779, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the free base of 6′-fluoro-4′,9′-dihydro-N-(4-methoxybenzyl)-4-benzyl-spiro[cyclohexane-1,1′(3′H)-pyrano[3,4-b]indol]-4-amine citrate (200 mg, 0.4 mmol) in tetrahydrofuran (20 ml) and methanol (20 ml) was mixed with 10% palladium on activated carbon (40 mg) and hydrogenated for 7 h under 3 bar and at 40° C. Then the reaction mixture was filtered through a pleated filter, the filter residue was washed with methanol and the filtrate was concentrated to small volume under vacuum. The crude product (186 mg) was purified by flash chromatography (20 g, 21×2 cm) with methanol. Yield: 136 mg (64%), beige-coloured solid. Melting point 198-205° C. (decomposition).

Workup

  1. filtrationThen the reaction mixture was filtered through a pleated filter
  2. washthe filter residue was washed with methanol
  3. concentrationthe filtrate was concentrated to small volume under vacuum
  4. customThe crude product (186 mg) was purified by flash chromatography (20 g, 21×2 cm) with methanol

Sources & evidence

ORD record
ord-e7944de3426948a6977ace355ccef918
Source dataset
uspto-grants-2011_06
Patent number
US07960404B2

Reaction notes

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