HCID 66894749, compound → HCID 59736751, compound

HRID 252827Notes

Reaction equation

HRID 252827 reaction equation
COC1C=C(N[CH2:12][C:13]2[CH:36]=[CH:35][C:16]([C:17]([NH:19][C:20]3[CH:25]=[C:24]([CH:26]=[CH:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:23]=[CH:22][C:21]=3[NH2:34])=[O:18])=[CH:15][CH:14]=2)C=CC=1OC>CO.C(OCC)(=O)C.[Pd]>[NH2:34][C:21]1[CH:22]=[CH:23][C:24]([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:25][C:20]=1[NH:19][C:17](=[O:18])[C:16]1[CH:15]=[CH:14][C:13]([CH3:12])=[CH:36][CH:35]=1

Participants

5

Reactant 1

HCID 66894749HCID 66894749, compound

Product 1

HCID 59736751HCID 59736751, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a degassed solution of compound 127 (100 mg, 0.209 mmol) in a mixture of methanol and ethyl acetate (1:1) was added was added a catalytic amount of 10% palladium on charcoal and the mixture was put under H2 atmosphere (latm) and stirred for 1 h and filtered through celite and the filtrate was concentrated in vacuo. The mixture was separated by flash chromatography on silica gel using EtOAc/Hexanes with increasing polarity (40:60 to 60:40) as the eluent. The least polar compound 129 was isolated as a white solid (31 mg, 31% yield) and the most polar compound was further purified by crystallization from a mixture of ethyl acetate and hexanes affording compound 128 as light beige crystals (18 mg, 18% yield).

Workup

  1. additionwas added
  2. filtrationfiltered through celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe mixture was separated by flash chromatography on silica gel
  5. temperaturewith increasing polarity (40:60 to 60:40) as the eluent

Sources & evidence

ORD record
ord-5bd98fa810fb489ea6f0ed014cd529ca
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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