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

HRID 1890773ノート

反応式

HRID 1890773 の反応式
[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]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 801724-Cyanobenzoyl chlorideHCID 67370777HCID 67370777、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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.

出典と根拠

ORDレコード
ord-11ae18646b0e4ecba4a41d04ad6a14b6
出典データセット
uspto-grants-2013_08
特許番号
US08507490B2

反応ノート

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