Cyclopropylamine → HCID 59536381, compound

HRID 445352Notes

Reaction equation

HRID 445352 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[F:13][C:14]([F:32])([F:31])[C:15]1[CH:20]=[CH:19][C:18]([C@@H:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:24][CH2:23][NH:22]2)=[CH:17][CH:16]=1.C([N:36]([CH:39]([CH3:41])[CH3:40])CC)(C)C.C1(N)CC1>C(Cl)Cl.O>[CH:39]1([NH:36][C:5]([N:22]2[CH2:23][CH2:24][C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:21]2[C:18]2[CH:17]=[CH:16][C:15]([C:14]([F:13])([F:31])[F:32])=[CH:20][CH:19]=2)=[O:11])[CH2:41][CH2:40]1

Participants

7

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 28293305(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 59536381HCID 59536381, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of triphosgene (0.05 mL, 0.4 mmol) in DCM (1 mL) at 0° C. was added a mixture of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (0.200 g, 0.7 mmol) and diisopropylethylamine (0.1 mL, 0.8 mmol) in DCM (1 mL). After stirring at 0° C. in 30 min, cyclopropylamine (0.04 mL, 0.7 mmol) was added and the mixture was continued to stir at RT for 24 h. H2O was added and layers were separated. The organic extracts were dried over MgSO4, concentrated and purified by ISCO (20% EtOAc/hexanes) to give the white solid title compound. MS (ESI, positive ion) m/z: 361 (M+1).

Workup

  1. stirringto stir at RT for 24 h
  2. customlayers were separated
  3. dry with materialThe organic extracts were dried over MgSO4
  4. concentrationconcentrated
  5. custompurified by ISCO (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d49f8f0b69eb4bd09bd9320d2e79d9f0
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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