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Hydrochloric Acid → HCID 68903775, 화합물

HRID 1986303
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HRID 1986303 반응식
[CH:1]1([NH:4][C:5]([C:7]2[C:15]3[CH:14]=[C:13]([C:16]4[C:21]([Cl:22])=[CH:20][N:19]=[C:18]([NH:23][CH2:24][CH2:25][CH2:26][N:27]5[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]5)[N:17]=4)[S:12][C:11]=3[C:10]([O:34]C)=[CH:9][CH:8]=2)=[O:6])[CH2:3][CH2:2]1.C(S)C.[H-].[Na+].Cl>CN(C=O)C.O>[CH:1]1([NH:4][C:5]([C:7]2[C:15]3[CH:14]=[C:13]([C:16]4[C:21]([Cl:22])=[CH:20][N:19]=[C:18]([NH:23][CH2:24][CH2:25][CH2:26][N:27]5[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]5)[N:17]=4)[S:12][C:11]=3[C:10]([OH:34])=[CH:9][CH:8]=2)=[O:6])[CH2:2][CH2:3]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 68857366HCID 68857366, 화합물

생성물 1

HCID 68903775HCID 68903775, 화합물수율 24%

시약·촉매·용매 2

HCID 962Water용매
HCID 6228
Dimethylformamide
용매

반응 조건

온도
110 °C

실험 절차

To a solution of 2-{5-chloro-2-[3-(4-methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-7-methoxybenzo[b]thiophene-4-carboxylic acid cyclopropylamide (500 mg, 0.970 mmol) and ethanethiol (0.718 mL, 9.71 mmol) in dry DMF (10 mL) is added in one portion sodium hydride (388 mg, 9.71 mmol) at 0° C. The mixture is stirred for 5 minutes and heated to 110° C. in a preheated oil bath for 10 minutes. The mixture is cooled to room temperature and a solution of HCl (12%, 3.5 mL) is added. The mixture is diluted with water (100 mL) and concentrated. The residue is diluted with MeOH and filtered off. The filtrate is purified on silica gel, eluting with dichloromethane in MeOH 90:10 to 60:40, to give the title compound as a yellow solid (116 mg, 24% yield). ES+(m/z) 501 (35Cl) and 503 (37Cl) [M+H].

후처리

  1. temperatureThe mixture is cooled to room temperature
  2. concentrationconcentrated
  3. additionThe residue is diluted with MeOH
  4. filtrationfiltered off
  5. customThe filtrate is purified on silica gel
  6. washeluting with dichloromethane in MeOH 90:10 to 60:40

출처 및 근거

ORD 기록
ord-3bf05187856646e88359975d6f0df49b
출처 데이터셋
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07547691B2

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