1,3-Dichloroacetone → 4-[(4-{[(6-Amino-3,5-dicyano-4-{4-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]phenyl}pyridin-2-yl)thio]methyl}-1,3-thiazol-2-yl)amino]benzoic acid

HRID 2362809

反応式

HRID 2362809 の反応式
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH2:13])=[S:12])=[CH:6][CH:5]=1)([OH:3])=[O:2].Cl[CH2:15][C:16]([CH2:18]Cl)=O.[NH2:20][C:21]1[C:26]([C:27]#[N:28])=[C:25]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH:37]3[CH2:41][O:40][C:39]([CH3:43])([CH3:42])[O:38]3)=[CH:31][CH:30]=2)[C:24]([C:44]#[N:45])=[C:23]([SH:46])[N:22]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:20][C:21]1[N:22]=[C:23]([S:46][CH2:18][C:16]2[N:13]=[C:11]([NH:10][C:7]3[CH:6]=[CH:5][C:4]([C:1]([OH:3])=[O:2])=[CH:9][CH:8]=3)[S:12][CH:15]=2)[C:24]([C:44]#[N:45])=[C:25]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH:37]3[CH2:41][O:40][C:39]([CH3:42])([CH3:43])[O:38]3)=[CH:31][CH:30]=2)[C:26]=1[C:27]#[N:28]

参加物

6

反応物 4

HCID 107931,3-DichloroacetoneHCID 516892Sodium BicarbonateHCID 7362164-Thioureidobenzoic acidHCID 178431437HCID 178431437、化合物

生成物 1

HCID 866243334-[(4-{[(6-Amino-3,5-dicyano-4-{4-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]phenyl}pyridin-2-yl)thio]methyl}-1,3-thiazol-2-yl)amino]benzoic acid

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

177 mg (0.90 mmol) of 4-carboxyphenylthiourea and 111 mg (0.87 mmol) of 1,3-dichloroacetone are dissolved in 3 ml of DMF, and the reaction solution is stirred at 100° C. for 60 min. After cooling, 230 mg (0.60 mmol) of the compound from Example 3A and 151 mg (1.80 mmol) of sodium bicarbonate are added, and the mixture is stirred at RT for a further 16 h. The reaction mixture is purified directly by preparative HPLC chromatography (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

後処理

  1. temperatureAfter cooling
  2. stirringthe mixture is stirred at RT for a further 16 h
  3. customThe reaction mixture is purified directly by preparative HPLC chromatography (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

出典と根拠

ORDレコード
ord-e44f1fb762ea4f54bf275d9b7de39cfd
出典データセット
uspto-grants-2014_04
特許番号
US08691850B2

関連ノート

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