HCID 178523838, compound → HCID 178523837, compound

HRID 1403163Notes

Reaction equation

HRID 1403163 reaction equation
[F:1][CH:2]([F:51])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([O:20][C@H:21]3[CH2:26][CH2:25][C@H:24]([N:27]4[CH2:31][CH2:30][C@H:29]([NH:32][C:33](=[O:45])[O:34][CH2:35][CH2:36][O:37]CC5C=CC=CC=5)[C:28]4=[O:46])[CH2:23][CH2:22]3)[CH:9]=2)[C:6]2[CH:47]=[CH:48][CH:49]=[CH:50][C:5]=2[N:4]=1>CO.[C].[Pd]>[F:51][CH:2]([F:1])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[N:11]=[C:10]([O:20][C@H:21]3[CH2:22][CH2:23][C@H:24]([N:27]4[CH2:31][CH2:30][C@H:29]([NH:32][C:33](=[O:45])[O:34][CH2:35][CH2:36][OH:37])[C:28]4=[O:46])[CH2:25][CH2:26]3)[CH:9]=2)[C:6]2[CH:47]=[CH:48][CH:49]=[CH:50][C:5]=2[N:4]=1

Participants

4

Reactant 1

HCID 178523838HCID 178523838, compound

Product 1

HCID 178523837HCID 178523837, compoundYield 40.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(benzyloxy)ethyl {(3S)-1-[trans-4-({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}oxy)cyclohexyl]-2-oxopyrrolidin-3-yl}carbamate (84 mg) in methanol (1 mL) was added 10% palladium-carbon (50% wet) (84 mg), followed by stirring at room temperature overnight at 3 atm under a hydrogen atmosphere. The catalyst was removed and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (chloroform:methanol=100:0-92:8) to obtain 2-hydroxyethyl {(3S)-1-[trans-4-({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}oxy)cyclohexyl]-2-oxopyrrolidin-3-yl}carbamate (30 mg).

Workup

  1. customThe catalyst was removed
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (chloroform:methanol=100:0-92:8)

Sources & evidence

ORD record
ord-3e5550f550f44391bb169040ee03e982
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

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