Trifluoroacetic acid → HCID 86603409, compound

HRID 1994476Notes

Reaction equation

HRID 1994476 reaction equation
[NH2:1][CH:2]([C:34]1[CH:39]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:37]=[C:36]([C:44]([F:47])([F:46])[F:45])[CH:35]=1)[CH2:3][N:4]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[C:23]1[CH:28]=[C:27]([CH:29]([CH3:31])[CH3:30])[CH:26]=[CH:25][C:24]=1[O:32][CH3:33])C(=O)OC(C)(C)C.FC(F)(F)C1C=C(C(NC(=O)OC(C)(C)C)CNCC2C=C(C(F)(F)F)C=CC=2C2C=C(C(C)C)C=CC=2OC)C=C(C(F)(F)F)C=1.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[F:41][C:40]([F:42])([F:43])[C:38]1[CH:39]=[C:34]([CH:2]([NH2:1])[CH2:3][NH:4][CH2:12][C:13]2[CH:18]=[C:17]([C:19]([F:20])([F:21])[F:22])[CH:16]=[CH:15][C:14]=2[C:23]2[CH:28]=[C:27]([CH:29]([CH3:31])[CH3:30])[CH:26]=[CH:25][C:24]=2[O:32][CH3:33])[CH:35]=[C:36]([C:44]([F:45])([F:47])[F:46])[CH:37]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 86603410HCID 86603410, compoundHCID 86620315HCID 86620315, compound

Product 1

HCID 86603409HCID 86603409, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 283.5 mg (0.418 mmol) of the mixture of tert-butyl {2-amino-2-[3,5-bis(trifluoromethyl)phenyl]ethyl}{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate and tert-butyl [1-[3,5-bis(trifluoromethyl)phenyl]-2-({[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}amino)ethyl]carbamate in CH2Cl2 (15 mL) was added TFA (1.5 mL). The reaction was stirred at room temperature for 5 hours and then poured into 1 N NaOH (50 mL). The mixture was extracted with CH2Cl2 (3×50 mL) and the organic extracts were combined, dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography with 5 to 10% MeOH/CH2Cl2 gave 1-[3,5-bis(trifluoromethyl)phenyl]-N2-{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}ethane-1,2-diamine. Rf=0.46 (10% MeOH/CH2Cl2). LCMS=579.2 (M+1)+. 1H NMR (CD2Cl2, 500 MHz) δ 7.83 (s, 2H), 7.77 (s, 2H), 7.55 (d, J=7.8 Hz, 1H), 7.31 (d, J=8.1 Hz, 1H), 7.24 (dd, J=8.4, 2.3 Hz, 1H), 6.99 (d, J=2.0 Hz, 1H), 6.92 (d, J=8.5 Hz, 1H), 4.06 (m, 1H), 3.59-3.76 (m, 2H), 3.69 (s, 3H), 2.88 (m, 1H), 2.67 (dd, J=11.9, 4.3 Hz, 1H), 2.51 (m, 1H), 1.22 (d, J=6.9 Hz, 6H).

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (3×50 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the residue by flash chromatography with 5 to 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-41c51ff4c40843d492d57e51717fd56b
Source dataset
uspto-grants-2010_01
Patent number
US07652049B2

Reaction notes

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