2-Bromoethanol → 3-{5-Amino-4-[3-(2-bromo-ethoxy)-benzoyl]-pyrazol-1-yl}-N-cyclopropyl-4-methylbenzamide

HRID 884814

反応式

HRID 884814 の反応式
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:10]([NH:12][CH:13]2[CH2:15][CH2:14]2)=[O:11])[N:5]=[CH:4][C:3]=1[C:20](=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=1.[Br:29][CH2:30][CH2:31]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OCC)=O)=NC(OCC)=O.[NH4+].[Cl-]>C1COCC1>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:10]([NH:12][CH:13]2[CH2:14][CH2:15]2)=[O:11])[N:5]=[CH:4][C:3]=1[C:20](=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:31][CH2:30][Br:29])[CH:22]=1

参加物

7

反応物 5

HCID 108982-BromoethanolHCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 112458363-[5-amino-4-(3-hydroxy-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methylbenzamide

生成物 1

HCID 580889463-{5-Amino-4-[3-(2-bromo-ethoxy)-benzoyl]-pyrazol-1-yl}-N-cyclopropyl-4-methylbenzamide収率 59.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 3-[5-amino-4-(3-hydroxy-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamide (472 mg, 1.26 mmol) in THF (dry, 20 mL) at 0° C. was added of 2-bromoethanol (785 mg, 6.3 mmol), PPh3 (1.3 g, 5.04 mmol) and diethyl azodicarboxylate (877 mg, 5.04 mmol) and the mixture was stirred at room temperature for 72 h. An aqueous solution of NH4Cl was added then the THF layer was isolated. The aqueous layer was extracted by EtOAc. The combined organic phase was washed by brine, purified by preparatory HPLC, to provide the product as a white solid (360 mg, 59%). HPLC (4 minute 10-90 gradient) tR 2.72 min; MS m/z 483.14/485.09 [M+H]+.

後処理

  1. extractionThe aqueous layer was extracted by EtOAc
  2. washThe combined organic phase was washed by brine
  3. custompurified by preparatory HPLC

出典と根拠

ORDレコード
ord-9c8515fca8464af9af822e4292aa122e
出典データセット
uspto-grants-2012_08
特許番号
US08242117B2

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