Dimethylformamide → Cyclopentanecarboxylic acid [(3-chloropyrazin-2-yl)-(4-phenoxyphenyl)-methyl]-amide

반응식

[Cl:1][C:2]1[C:3]([CH:8]([NH2:22])[C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][N:7]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=N[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN(C=[O:58])C>>[Cl:1][C:2]1[C:3]([CH:8]([NH:22][C:41]([CH:46]2[CH2:42][CH2:43][CH2:44][CH2:45]2)=[O:58])[C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:13][CH:14]=2)=[N:4][CH:5]=[CH:6][N:7]=1

참가 물질

반응물 4

HCID 6228Dimethylformamide

HCID 81531Diisopropylethylamine

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

HCID 59341168HCID 59341168, 화합물

생성물 1

HCID 86636031Cyclopentanecarboxylic acid [(3-chloropyrazin-2-yl)-(4-phenoxyphenyl)-methyl]-amide수율 81.7%

실험 절차

In a 10 mL flask were added C-(3-chloropyrazin-2-yl)-C-(4-phenoxyphenyl)-methylamine (75 mg, 0.24 mmol), DIEA (0.38 mL, 0.0022 mol), TBTU (0.12 g, 0.00036 mol) and DMF (4 mL, 0.05 mol) and the reaction mixture is stirred at rt overnight. Reaction mixture was concentrated in vacuo and washed with sat NaHCO3, brine extracting with DCM. The organic layer was concentrated to give a dark yellow solid. Purification by prep TLC using 50% EtOAc: hexanes afforded 80 mg of the title compound as an off white solid. MS (ES+): m/z 407.86 (50)[MH+]. HPLC: tR=3.75 min (Open Lynx, polar—5 min).