Acetic Acid → 3,5-dimethyl-4-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyrazole-1-carboxylic acid 4-methoxy-benzylamide

HRID 1952112ノート

反応式

HRID 1952112 の反応式
C(OC([N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10]([CH2:17][C:18]2[C:19]([CH3:24])=[N:20][NH:21][C:22]=2[CH3:23])=[CH:9]1)=O)(C)(C)C.[N:25]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)=[C:26]=[O:27].C(O)(=O)C>ClCCl>[CH3:36][O:35][C:32]1[CH:33]=[CH:34][C:29]([CH2:28][NH:25][C:26]([N:21]2[C:22]([CH3:23])=[C:18]([CH2:17][C:10]3[C:11]4[C:12](=[N:13][CH:14]=[CH:15][CH:16]=4)[NH:8][CH:9]=3)[C:19]([CH3:24])=[N:20]2)=[O:27])=[CH:30][CH:31]=1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 187910Isocyanic acid, p-methoxybenzyl-HCID 595933443-(3,5-Dimethyl-1H-pyrazol-4-ylmethyl)-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 249535763,5-dimethyl-4-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyrazole-1-carboxylic acid 4-methoxy-benzylamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

3-(3,5-dimethyl-1H-pyrazol-4-ylmethyl)-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester (514, 10 mg, 0.03 mmol) was dissolved in dichloromethane (0.5 mL). 1,8-Diazabicylo[5.4.0]unde-7-ene (6 mg, 0.04 mmol) was added. 1-Isocyanatomethyl-4-methoxy-benzene (545, 6.5 mg, 0.04 mmol) was added. The reaction was allowed to proceed at room temperature for 30 minutes. Acetic acid (0.2 mL) was added to the reaction. The solvents were removed under reduced pressure. The residue was dissolved in dimethyl sulfoxide (0.2 mL) and purified by reverse phase HPLC on a Phenomenex column (50 mm×10 mm ID), eluting with water with 0.1% trifluoroacetic acid and 20-100% acetonitrile with 0.1% trifluoroacetic acid over 16 minutes at a flow rate of 6 mL/minute to provide the desired compound P-0135. MS (ESI) [M+H+]+=390.3.

後処理

  1. customThe solvents were removed under reduced pressure
  2. dissolutionThe residue was dissolved in dimethyl sulfoxide (0.2 mL)
  3. custompurified by reverse phase HPLC on a Phenomenex column (50 mm×10 mm ID)
  4. washeluting with water with 0.1% trifluoroacetic acid and 20-100% acetonitrile with 0.1% trifluoroacetic acid over 16 minutes at a flow rate of 6 mL/minute

出典と根拠

ORDレコード
ord-ede87c38e91d43159eb58db9664d3f7e
出典データセット
uspto-grants-2013_03
特許番号
US08404700B2

反応ノート

読み込み中…