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1,2-Dichloroethane → 3-Chloro-6-methyl-pyridazine-4-carboxylic acid [3-(4-tert-butylcarbamoyl-piperidin-1-ylmethyl)-phenyl]-amide

HRID 1486750
ノート
印刷プレビュー

反応式

HRID 1486750 の反応式
[C:1]([NH:5][C:6]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:22][C:23]1[N:24]=[N:25][C:26]([CH3:32])=[CH:27][C:28]=1[C:29](O)=[O:30].C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([NH:5][C:6]([CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][C:15]2[CH:16]=[C:17]([NH:21][C:29]([C:28]3[CH:27]=[C:26]([CH3:32])[N:25]=[N:24][C:23]=3[Cl:22])=[O:30])[CH:18]=[CH:19][CH:20]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 111,2-DichloroethaneHCID 265992153-Chloro-6-methylpyridazine-4-carboxylic acidHCID 867065251-(3-Amino-benzyl)-piperidine-4-carboxylic acid tert-butylamide

生成物 1

HCID 1185218653-Chloro-6-methyl-pyridazine-4-carboxylic acid [3-(4-tert-butylcarbamoyl-piperidin-1-ylmethyl)-phenyl]-amide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine
触媒
HCID 6344Dichloromethane溶媒

実験手順

A solution of 1-(3-amino-benzyl)-piperidine-4-carboxylic acid tert-butylamide BB-4 (400 mg, 1.4 mmol) in DCM (15 mL) is treated successively with 3-chloro-6-methyl-pyridazine-4-carboxylic acid (239 mg, 1.4 mmol), EDC (344 mg, 1.8 mmol) and DMAP (25.3 mg, 0.207 mmol) at RT overnight. The reaction mixture is washed twice with sat.aq. NaHCO3 (15 mL). The aqueous phase is extracted twice with DCM (2×10 mL). The combined organic layers are dried over MgSO4 and filtered. The solvent is evaporated under reduced pressure. The residue is purified by prep HPLC E delivering the title compound (53 mg, 36%) as a light brownish powder, LC-MS A: tR=0.60 min; [M+H]+=444.12.

後処理

  1. washThe reaction mixture is washed twice with sat.aq
  2. extractionThe aqueous phase is extracted twice with DCM (2×10 mL)
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. filtrationfiltered
  5. customThe solvent is evaporated under reduced pressure
  6. customThe residue is purified by prep HPLC E

出典と根拠

ORDレコード
ord-7954e4882bd14dbc9cc23f7fd0fa971a
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09428456B2

反応ノート

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