Formaldehyde → 1-(4-Chloro-5,7-difluoro-3-methylquinolin-2-yl)-4-methylpiperazin-2-one

HRID 1431433

반응식

HRID 1431433 반응식
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][C:15]2=[O:20])[C:3]=1[CH3:21].C=O.[C:24](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([BH3-])#N.[Na+]>ClC(Cl)C.C(Cl)Cl.O.CO>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([N:14]2[CH2:19][CH2:18][N:17]([CH3:24])[CH2:16][C:15]2=[O:20])[C:3]=1[CH3:21]

참가 물질

9

반응물 4

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 5049666Sodium triacetoxyborohydrideHCID 596313891-(4-Chloro-5,7-difluoro-3-methylquinolin-2-yl)piperazin-2-one

생성물 1

HCID 596313171-(4-Chloro-5,7-difluoro-3-methylquinolin-2-yl)-4-methylpiperazin-2-one

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 6344Dichloromethane용매HCID 63651,1-Dichloroethane용매

실험 절차

The 1-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)piperazin-2-one (52.0 mg, 0.167 mmol) and paraformaldehyde (5.01 mg, 0.167 mmol) were dissolved in 1.5 mL of a 2:1 dichloroethane:MeOH solution. The sodium triacetoxyborohydride (106 mg, 0.500 mmol) was added and the reaction mixture was stirred for 6.5 h. The reaction by LCMS had only progressed ˜30%. Some sodium cyanoborohydride (50 mg, 0.796 mmol) was added turning the mixture into a solution again and stirred overnight. The reaction was then diluted with DCM and water. The layers were separated and the organic layer was washed with brine (1×10 mL) and dried over magnesium sulfate to give crude 1-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)-4-methylpiperazin-2-one. Mass Spectrum (ESI) m/e=312.1 (M+1).

후처리

  1. customThe reaction by LCMS
  2. stirringstirred overnight
  3. customThe layers were separated
  4. washthe organic layer was washed with brine (1×10 mL)
  5. dry with materialdried over magnesium sulfate

출처 및 근거

ORD 기록
ord-59238b8b1a8a4eb196186884b4b7af87
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940724B2

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