1-Phenethylamine, (-)- → HCID 86600301, compound

HRID 729525Notes

Reaction equation

HRID 729525 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH:18]4[CH2:20][CH:15]3[CH2:16][N:17]4[CH2:21][CH:22]([F:24])[F:23])[N:11]3[CH:25]=[CH:26][N:27]=[C:10]3[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[CH3:28][C@H:29]([NH2:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+]>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[F:23][CH:22]([F:24])[CH2:21][N:17]1[CH2:16][C@@H:15]2[CH2:20][C@H:18]1[CH2:19][N:14]2[C:12]1[N:11]2[CH:25]=[CH:26][N:27]=[C:10]2[CH:9]=[C:8]([C:6]2([NH:36][C@H:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH3:28])[CH:5]=[CH:4][N:3]=[CH:2][CH2:7]2)[N:13]=1

Participants

8

Reactant 4

HCID 758181-Phenethylamine, (-)-HCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 86600302HCID 86600302, compound

Product 1

HCID 86600301HCID 86600301, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To an RBF was added 7-(2-chloro-pyridin-4-yl)-5-[5-(2,2-difluoro-ethyl)-2,5-diaza-bicyclo[2.2.1]hept-2-yl]-imidazo[1,2-c]pyrimidine (40 mg, 0.10 mmol), 1 mL toluene, and (S)-α-methylbenzylamine (0.015 mL, 0.11 mmol). The mixture was degassed by bubbling nitrogen through solution for 1 h. After Pd(OAc)2 (2 mg, 0.01 mmol), rac-BINAP (6 mg, 0.01 mmol), and NaOtBu (0.20 mg, 0.21 mmol) were added, the mixture was warmed up to 90° C. and stirred for 3 h under nitrogen. The mixture was cooled down to ambient temperature, diluted with 50 mL DCM, washed with 20 mL sat. NaHCO3, and dried over anhydrous Na2SO4. After purification by preparatory TLC, the title compound was obtained. MS (ES+): 476 (M+H)+.

Workup

  1. customThe mixture was degassed
  2. customby bubbling nitrogen through solution for 1 h
  3. temperatureThe mixture was cooled down to ambient temperature
  4. washwashed with 20 mL sat. NaHCO3
  5. dry with materialdried over anhydrous Na2SO4
  6. customAfter purification by preparatory TLC

Sources & evidence

ORD record
ord-31ebb0cdcca54c7eab96ddcb83de9ff0
Source dataset
uspto-grants-2009_09
Patent number
US07582631B2

Reaction notes

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