Hydrochloric Acid → 4-Cyano-N-(1-(6-(4-cyanophenyl)-4,5-dimethylpyridazin-3-yl)piperidin-4-yl)-N-methylbenzamide hydrochloride

HRID 1890773노트

반응식

HRID 1890773 반응식
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([N:9]2[CH2:14][CH2:13][CH:12]([NH:15][CH3:16])[CH2:11][CH2:10]2)[N:5]=[N:4][C:3]=1[C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1.C(N(CC)CC)C.[C:32]([C:34]1[CH:42]=[CH:41][C:37]([C:38]([Cl:40])=[O:39])=[CH:36][CH:35]=1)#[N:33].Cl>C(Cl)Cl.CO>[ClH:40].[C:32]([C:34]1[CH:42]=[CH:41][C:37]([C:38]([N:15]([CH:12]2[CH2:13][CH2:14][N:9]([C:6]3[N:5]=[N:4][C:3]([C:17]4[CH:18]=[CH:19][C:20]([C:21]#[N:22])=[CH:23][CH:24]=4)=[C:2]([CH3:1])[C:7]=3[CH3:8])[CH2:10][CH2:11]2)[CH3:16])=[O:39])=[CH:36][CH:35]=1)#[N:33]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 801724-Cyanobenzoyl chlorideHCID 67370777HCID 67370777, 화합물

생성물 1

HCID 462033944-Cyano-N-(1-(6-(4-cyanophenyl)-4,5-dimethylpyridazin-3-yl)piperidin-4-yl)-N-methylbenzamide hydrochloride수율 95.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

Treat a solution of 4-(4,5-dimethyl-6-(4-(methylamino)piperidin-1-yl)pyridazin-3-yl)benzonitrile (90 mg, 0.28 mmol) and triethylamine (0.12 mL, 0.84 mmol) in CH2Cl2 (2.8 mL) with 4-cyanobenzoyl chloride (56 mg, 0.34 mmol). Stir the reaction at ambient temperature overnight. Wash with H2O and separate the layers. Directly purify the organic layer by flash silica gel chromatography (gradient of 0 to 2% 2 M NH3/MeOH in CH2Cl2). Concentrate to afford a white solid. Dissolve the material in MeOH and add 1.1 eq of methanolic HCl (preform by dripping acetyl chloride into MeOH). Concentrate the mixture under a stream of N2 gas and dry the residue in a vacuum oven at 45° C. to obtain the title compound as yellow solid (130 mg, 95%). ES/MS m/z 451.2 (M+1).

후처리

  1. customthe reaction at ambient temperature overnight
  2. washWash with H2O
  3. customseparate the layers
  4. customDirectly purify the organic layer by flash silica gel chromatography (gradient of 0 to 2% 2 M NH3/MeOH in CH2Cl2)
  5. concentrationConcentrate
  6. customto afford a white solid
  7. concentrationConcentrate the mixture under a stream of N2 gas
  8. customdry the residue in a vacuum oven at 45° C.

출처 및 근거

ORD 기록
ord-11ae18646b0e4ecba4a41d04ad6a14b6
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507490B2

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