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

반응식

HRID 2362809 반응식
[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]

참가 물질

6

반응물 4

HCID 107931,3-DichloroacetoneHCID 516892Sodium BicarbonateHCID 7362164-Thioureidobenzoic acidHCID 178431437HCID 178431437, 화합물

생성물 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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e44f1fb762ea4f54bf275d9b7de39cfd
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691850B2

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