1-Phenethylamine, (-)- → HCID 12147075, compound

HRID 2415690Notes

Reaction equation

HRID 2415690 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16](=[O:17])[N:11]3[CH2:12][CH:13]=[CH:14][CH2:15][N:10]3[CH:9]2[C:18]2[CH:23]=[CH:22][N:21]=[C:20](S(C)(=O)=O)[N:19]=2)=[CH:4][CH:3]=1.[CH3:28][C@H:29]([NH2:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16](=[O:17])[N:11]3[CH2:12][CH:13]=[CH:14][CH2:15][N:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:36][C@H:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH3:28])[N:19]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 758181-Phenethylamine, (-)-HCID 22636403HCID 22636403, compound

Product 1

HCID 12147075HCID 12147075, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

2-(4-Fluorophenyl)-3-(2-methanesulfonyl-pyrimidin-4-yl)-2,3,5,8-tetrahydro-pyrazolo[1,2-a]pyridazin-1-one, 12, (0.9 g, 2.3 mmol) is dissolved in toluene (18 mL) and (S)-(−)-α-methylbenzylamine (10.5 mL, 81.6 mmol) added. The resulting mixture is heated to 140° C. for 12 hours, cooled, and the solvent removed in vacuo. The resulting crude product is purified over silica (1:1 EtOAc/hexanes) to afford 0.8 g (80% yield) of the desired product as a red sticky solid.

Workup

  1. temperaturecooled
  2. customthe solvent removed in vacuo
  3. customThe resulting crude product is purified over silica (1:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-1fe84acc82814402a7e1c2c338cadf57
Source dataset
uspto-grants-2004_11
Patent number
US06821971B2

Reaction notes

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