(3-Benzyloxy-5-trifluoromethyl-benzyl)-(5'-isopropyl-2'-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amine → HCID 86626897, compound

HRID 604157Notes

Reaction equation

HRID 604157 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:48]=[C:49]([C:51]([F:54])([F:53])[F:52])[CH:50]=1)[CH2:12][N:13]([CH2:26][C:27]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:28]=1[C:37]1[CH:42]=[C:41]([CH:43]([CH3:45])[CH3:44])[CH:40]=[CH:39][C:38]=1[O:46][CH3:47])[C:14]1[N:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:16][N:15]=1)C1C=CC=CC=1>CO.[C].[Pd]>[CH:43]([C:41]1[CH:40]=[CH:39][C:38]([O:46][CH3:47])=[C:37]([C:28]2[CH:29]=[CH:30][C:31]([C:33]([F:36])([F:35])[F:34])=[CH:32][C:27]=2[CH2:26][N:13]([CH2:12][C:11]2[CH:10]=[C:9]([OH:8])[CH:50]=[C:49]([C:51]([F:54])([F:52])[F:53])[CH:48]=2)[C:14]2[N:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:16][N:15]=2)[CH:42]=1)([CH3:45])[CH3:44]

Participants

4

Reactant 1

HCID 86626896(3-Benzyloxy-5-trifluoromethyl-benzyl)-(5'-isopropyl-2'-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amine

Product 1

HCID 86626897HCID 86626897, compoundYield 51.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

(3-Benzyloxy-5-trifluoromethyl-benzyl)-(5′-isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amine (215 mg) is dissolved in methanol (10.5 ml), and thereto is added 10% palladium-carbon and the mixture is stirred under hydrogen atmosphere at room temperature for 1 hour. 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=4:1→1:2, and chloroform:methanol 19:1→9:1) to give 3-{[(5′-isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amino]-methyl}-5-trifluoromethyl-phenol (98 mg). MS (m/z): 661 [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=4:1→1:2, and chloroform:methanol 19:1→9:1)

Sources & evidence

ORD record
ord-0bc42bef55a94299ac8a63d7efda1491
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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