Hydrochloric Acid → 2-(4-fluorophenyl)-3-(isopropylamino)-1-(4-((S)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl)propan-1-one dihydrochloride

HRID 625058노트

반응식

HRID 625058 반응식
[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:22]([N:24]2[CH2:29][CH2:28][N:27]([C:30]3[C:31]4[C@H:38]([CH3:39])[S:37][CH2:36][C:32]=4[N:33]=[CH:34][N:35]=3)[CH2:26][CH2:25]2)=[O:23])[CH2:10][N:11]([CH:19]([CH3:21])[CH3:20])C(=O)OC(C)(C)C)=[CH:5][CH:4]=1>CCOCC.C(Cl)Cl>[ClH:1].[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH2:10][NH:11][CH:19]([CH3:21])[CH3:20])[C:22]([N:24]2[CH2:29][CH2:28][N:27]([C:30]3[C:31]4[C@H:38]([CH3:39])[S:37][CH2:36][C:32]=4[N:33]=[CH:34][N:35]=3)[CH2:26][CH2:25]2)=[O:23])=[CH:5][CH:4]=1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 67459971tert-butyl 2-(4-fluorophenyl)-3-(4-((S)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate

생성물 1

HCID 249497592-(4-fluorophenyl)-3-(isopropylamino)-1-(4-((S)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl)propan-1-one dihydrochloride수율 63%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

HCl (4N in dioxane) was added to a solution of tert-butyl 2-(4-fluorophenyl)-3-(4-((S)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate (50 mg, 0.092 mmol) in Et2O (4 mL) and DCM (0.5 mL) at room temperature. The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated in vacuo. The residue was taken up into DCM (1 mL), and precipitated with Et2O (15 mL), and the solids were filtered under nitrogen to give 2-(4-fluorophenyl)-3-(isopropylamino)-1-(4-((S)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl)propan-1-one dihydrochloride (30 mg, 63% yield) as a mixture of 2 diastereomers. LCMS (APCI+) [M+H]+ 444.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customprecipitated with Et2O (15 mL)
  3. filtrationthe solids were filtered under nitrogen

출처 및 근거

ORD 기록
ord-6c083cdf8772492480cd189178552fa3
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303040B2

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