(S)-1-(2,4-Difluorophenyl)ethanamine → HCID 67152322, compound

HRID 1428191Notes

Reaction equation

HRID 1428191 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([C:10]2[CH:11]=[N:12][N:13]3[CH:18]=[CH:17][CH:16]=[N:15][C:14]=23)[CH:3]=1.[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[C@@H:27]([NH2:29])[CH3:28]>CN1C(=O)CCC1>[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[C@@H:27]([NH:29][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[N:12][N:13]3[CH:18]=[CH:17][CH:16]=[N:15][C:14]=23)[N:5]=[C:6]([S:8][CH3:9])[N:7]=1)[CH3:28]

Participants

4

Reactant 2

HCID 2060581(S)-1-(2,4-Difluorophenyl)ethanamineHCID 58268975HCID 58268975, compound

Product 1

HCID 67152322HCID 67152322, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A 7 ml NMP solution of 3-(6-chloro-2-(methylthio)pyrimidin-4-yl)pyrazolo[1,5-a]pyrimidine (7h, 1.30 g) and (S)-1-(2,4-difluoro-phenyl)ethanamine (1.47 g) was heated in a microwave reactor at 220° C. for 20 min. LC/MS indicated the major peak was the desired product. The reaction mixture was partitioned between ethyl acetate and sat. NH4OAc. The organic phase was dried with MgSO4, filtered and the solvent was removed under reduced pressure. The product was purified by chromatography (SiO2, EtOAc-Hex, 1:1) (1.09 g, 58.6% yield).

Sources & evidence

ORD record
ord-2d55575e489d4b5e846bc867470d3144
Source dataset
uspto-grants-2015_01
Patent number
US08937064B2

Reaction notes

Loading…