HCID 86626762, compound → HCID 86626761, compound

HRID 604002Notes

Reaction equation

HRID 604002 reaction equation
[CH2:1]([N:8](CC)[C:9]1[CH:46]=[CH:45][C:44]([C:47]([F:50])([F:49])[F:48])=[CH:43][C:10]=1[CH2:11][N:12]([CH2:28][C:29]1[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[C:31]([C:39]([F:42])([F:41])[F:40])[CH:30]=1)[C:13]1[N:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:15][N:14]=1)[C:2]1C=CC=CC=1>C(O)C.[C].[Pd]>[F:38][C:35]([F:36])([F:37])[C:33]1[CH:34]=[C:29]([CH:30]=[C:31]([C:39]([F:40])([F:41])[F:42])[CH:32]=1)[CH2:28][N:12]([CH2:11][C:10]1[CH:43]=[C:44]([C:47]([F:50])([F:49])[F:48])[CH:45]=[CH:46][C:9]=1[NH:8][CH2:1][CH3:2])[C:13]1[N:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:17][N:18]=1

Participants

4

Reactant 1

HCID 86626762HCID 86626762, compound

Product 1

HCID 86626761HCID 86626761, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Ethyl 4-{2-[[2-(benzyl-ethyl-amino)-5-trifluoromethyl-benzyl]-(3,5-bis-trifluoromethyl-benzyl)-amino]-pyrimidin-5-yloxy}-butyrate (4.07 g) is dissolved in ethanol (60 ml), and thereto is added 10% palladium-carbon (500 mg) and the mixture is stirred under hydrogen atmosphere at room temperature for 30 minutes. The catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (hexane:ethyl acetate=19:1→17:3) to give ethyl 4-{2-[(3,5-bis-trifluoromethyl-benzyl)-(2-ethylamino-5-trifluoromethyl-benzyl)-amino]-pyrimidin-5-yloxy}-butyrate (3.1 g). MS (m/z): 653 [M+H]+

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe resulting residue is purified by NH-silica gel column chromatography (hexane:ethyl acetate=19:1→17:3)

Sources & evidence

ORD record
ord-3cb479479da1407b8cd3fd0a0b28465d
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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