Isobutylamine → HCID 59536365, compound

HRID 445354Notes

Reaction equation

HRID 445354 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.Cl[C:31](OC1C=CC([N+]([O-])=O)=CC=1)=[O:32].[CH3:43][CH:44]([CH3:47])[CH2:45][NH2:46]>C1COCC1.O>[CH2:45]([NH:46][C:31]([N:10]1[CH2:11][CH2:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:9]1[C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:20])=[CH:8][CH:7]=1)=[O:32])[CH:44]([CH3:47])[CH3:43]

Participants

7

Reactant 4

HCID 6558IsobutylamineHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 28293305(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 59536365HCID 59536365, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (0.100 g, 0.36 mmol) and DIEA (0.082 mL, 0.47 mmol) in THF (2 mL) was added 4-nitrophenyl chloroformate (0.080 g, 0.40 mmol). The reaction mixture was stirred for 30 min, 2-methylpropan-1-amine (0.036 mL, 0.36 mmol) was added and stirring was continued for 14 h, then heated at reflux for 24 h, cooled, taken up in H2O, extracted with EtOAc (3×), dried over MgSO4, concentrated and purified by ISCO (20% EtOAc/hexanes) to give the title compound. MS (ESI, positive ion) m/z: 377 (M+1).

Workup

  1. stirringstirring
  2. waitwas continued for 14 h
  3. temperatureheated
  4. temperatureat reflux for 24 h
  5. temperaturecooled
  6. extractionextracted with EtOAc (3×)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. custompurified by ISCO (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c8fe7484af5b4143bd22dd9253eb294b
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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