HCID 178505055, compound → HCID 178505062, compound

HRID 272252Notes

Reaction equation

HRID 272252 reaction equation
C([N:8]([CH2:35][C@H:36]([OH:58])[CH2:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([O:45]CC2C=CC=CC=2)=[C:41]([NH:53][S:54]([CH3:57])(=[O:56])=[O:55])[CH:40]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:34]=[CH:33][C:18]([C:19]([NH:21][CH2:22][CH2:23][C:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[NH:26][CH:25]=3)=[O:20])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)C1C=CC=CC=1>C(O)C.O1CCCC1.[Pd]>[OH:58][C@H:36]([CH2:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[C:41]([NH:53][S:54]([CH3:57])(=[O:55])=[O:56])[CH:40]=1)[CH2:35][NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:34]=[CH:33][C:18]([C:19]([NH:21][CH2:22][CH2:23][C:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[NH:26][CH:25]=3)=[O:20])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 1

HCID 178505055HCID 178505055, compound

Product 1

HCID 178505062HCID 178505062, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 0.246 g (0.3 mmol) of trans-4-{4-[benzyl((2S)-3-{4-(benzyloxy)-3-[(methylsulfonyl)amino]phenoxy}-2-hydroxypropyl)amino]cyclohexyl}-N-[2-(1H-indol-3-yl)ethyl]benzamide and of 0.332 g of palladium-on-charcoal (10% Pd, 50% in water) in a mixture of 5.4 ml of ethanol and 4 ml of tetrahydrofuran is placed under hydrogen atmosphere and is stirred for 3 h. The catalyst is subsequently filtered off and the solvents are evaporated under reduced pressure. The title compound is obtained in the form of a white solid (0.076 g, 40%) after purification on silica gel (eluent: dichloromethane/methanol/aqueous ammonia 99/1/0.1 to 85/15/1.5 gradient in 30 min).

Workup

  1. filtrationThe catalyst is subsequently filtered off
  2. customthe solvents are evaporated under reduced pressure

Sources & evidence

ORD record
ord-16c75bb28c614f0eab88f86def840e6b
Source dataset
uspto-grants-2008_11
Patent number
US07453010B2

Reaction notes

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