반응 #77831

반응 방정식

benzamide

benzamide N-[2-[[(1S,2S)-2-[[(4-chlorophenyl)methyl]amino]cyclohexyl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide

formaldehyde

→

benzamide N-[2-[[(1S,2S)-2-[(4-chlorobenzyl)(methyl)amino]cyclohexyl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide

수율 93.0%

용매

THF

반응 조건

후처리

1. 1
   기타was quenched with NaHCO3 solution
2. 2
   추출This was extracted with EtOAc
3. 3
   건조The EtOAc was dried
4. 4
   농축concentrated
5. 5
   기타Reverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue

실험 절차

The title benzamide from Example 1 (21 mg) was dissolved in THF prior to the addition of Hunigs's base (0.01 mL). Next, 37% formaldehyde (0.017 mL) was added along with 4A molecular sieves. After 3 h, NaHB(OAc)3 (38 mg) was added. This mixture was stirred an additional 2 h before the reaction was quenched with NaHCO3 solution. This was extracted with EtOAc. The EtOAc was dried and concentrated. Reverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue provided the title benzamide N-[2-[[(1S,2S)-2-[(4-chlorobenzyl)(methyl)amino]cyclohexyl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide (10 mg). MS found: (M+H)+=482.3.

출처