Methyl {[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}[3-nitro-5-(trifluoromethyl)benzyl]carbamate → Methyl[3-amino-5-(trifluoromethyl)benzyl]{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

HRID 217512Notes

Reaction equation

HRID 217512 reaction equation
[CH3:1][O:2][C:3](=[O:41])[N:4]([CH2:19][C:20]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=1[C:30]1[CH:35]=[C:34]([CH:36]([CH3:38])[CH3:37])[CH:33]=[CH:32][C:31]=1[O:39][CH3:40])[CH2:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([N+:16]([O-])=O)[CH:7]=1>C1COCC1.O=[Pt]=O>[CH3:1][O:2][C:3](=[O:41])[N:4]([CH2:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([NH2:16])[CH:7]=1)[CH2:19][C:20]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=1[C:30]1[CH:35]=[C:34]([CH:36]([CH3:38])[CH3:37])[CH:33]=[CH:32][C:31]=1[O:39][CH3:40]

Participants

4

Reactant 1

HCID 11534401Methyl {[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}[3-nitro-5-(trifluoromethyl)benzyl]carbamate

Product 1

HCID 11699642Methyl[3-amino-5-(trifluoromethyl)benzyl]{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}[3-nitro-5-(trifluoromethyl)benzyl]carbamate (174 mg, 0.03 mmol) (Example 22) and PtO2 (10 mg) in THF (10 mL) was placed under hydrogen. The reaction was stirred at room temperature under hydrogen for two hours. The reaction was then diluted with hexanes (25 mL), loaded on a silica gel column, and purified with 15% EtOAc/hexanes to afford methyl[3-amino-5-(trifluoromethyl)benzyl]{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate. Rf=0.31 (25% EtOAc/hexanes). LCMS=555.3 (M+1)+. 1H NMR (CDCl3, 600 MHz) δ 7.59-6.28 (m, 9H), 4.48-3.62 (m, 12H), 2.87 (m, 1H), 1.22 (broad singlet, 6H).

Workup

  1. custompurified with 15% EtOAc/hexanes

Sources & evidence

ORD record
ord-ae97efbf221f405db20faa703831145b
Source dataset
uspto-grants-2012_06
Patent number
US08193365B2

Reaction notes

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