HCID 23365872, compound → HCID 178497910, compound

HRID 1723244Notes

Reaction equation

HRID 1723244 reaction equation
C([O:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([NH:18][C:19](=[O:26])[CH2:20][CH:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:15][CH:16]=2)[N:11]([CH2:27][C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][C:29]=2[O:38][CH3:39])[N:10]=1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[CH:21]1([CH2:20][C:19]([NH:18][C:14]2[CH:13]=[C:12]3[C:17]([C:9]([OH:8])=[N:10][N:11]3[CH2:27][C:28]3[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][C:29]=3[O:38][CH3:39])=[CH:16][CH:15]=2)=[O:26])[CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

4

Reactant 1

HCID 23365872HCID 23365872, compound

Product 1

HCID 178497910HCID 178497910, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 4-[3-benzyloxy-6-(2-cyclopentylacetamido)indazol-1-ylmethyl]-3-methoxybenzoate (BB) (5.0 g.), and palladium-on-carbon (5% w/w, 1.25 g.), in ethyl acetate (190 ml.), was hydrogenated at 1.1 bar for 7.5 hours. The catalyst was removed by filtration through diatomaceous earth, washing the filter cake with ethanol, the filtrate partially evaporated, and the residue allowed to crystallize to give the title compound (2.56 g., 62%), as a solid, m.p. 242°-245° C.

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. washwashing the filter cake with ethanol
  3. customthe filtrate partially evaporated
  4. customto crystallize

Sources & evidence

ORD record
ord-259597fb6ccb46339c5ac9136a5b2b9c
Source dataset
uspto-grants-1989_08
Patent number
US04859692

Reaction notes

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