Hydrochloric Acid → 1-(Piperidin-4-ylmethyl)-2-thioxo-1,2,3,5-tetrahydro-pyrrolo[3,2-d]pyrimidin-4-one

HRID 536087노트

반응식

HRID 536087 반응식
C(O[C:4]([N:6]=[C:7]=[S:8])=[O:5])C.C(OC([N:16]1[CH2:21][CH2:20][CH:19]([CH2:22][NH:23][C:24]2[CH:28]=[CH:27][NH:26][C:25]=2C(OCC)=O)[CH2:18][CH2:17]1)=O)(C)(C)C.[Na].Cl>C(Cl)Cl>[NH:16]1[CH2:17][CH2:18][CH:19]([CH2:22][N:23]2[C:24]3[CH:28]=[CH:27][NH:26][C:25]=3[C:4](=[O:5])[NH:6][C:7]2=[S:8])[CH2:20][CH2:21]1

참가 물질

6

반응물 4

HCID 313Hydrochloric Acid2회HCID 85320Ethyl isothiocyanatoformateHCID 5360545SodiumHCID 670684721-Boc-4-[(2-Ethoxycarbonyl-1H-pyrrol-3-ylamino)methyl]piperidine

생성물 1

HCID 116303361-(Piperidin-4-ylmethyl)-2-thioxo-1,2,3,5-tetrahydro-pyrrolo[3,2-d]pyrimidin-4-one수율 32.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Ethoxycarbonyl isothiocyanate (0.058 g, 0.44 mmol) was added to a stirred solution of 4-[(2-(ethoxycarbonyl)-1H-pyrrol-3-ylamino)-methyl]piperidine-1-carboxylic acid tert-butyl ester (0.156 g, 0.44 mmol) in CH2Cl2(2 mL) and the mixture was stirred at r.t. for 1 h. The solvent was removed in vacuo and the residue was taken up in ethanol (1 mL) containing sodium (0.015 g, 0.66 mmol). The resulting mixture was heated in a microwave reactor at 120° C. for 10 minutes. 6M HCl (0.5 mL) was added and the reaction mixture was heated again in the microwave at 100° C. for 3 minutes. The pH was adjusted to neutral pH with 2M HCl and the solution was concentrated in vacuo. The crude product was purified by preparative HPLC to give the title compound (0.038 g, 14%) as a white solid.

후처리

  1. customThe solvent was removed in vacuo
  2. temperatureThe resulting mixture was heated in a microwave reactor at 120° C. for 10 minutes
  3. temperaturethe reaction mixture was heated again in the microwave at 100° C. for 3 minutes
  4. concentrationthe solution was concentrated in vacuo
  5. customThe crude product was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-426b993ccc3a4b188b9dd8d695bf5d59
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859568B2

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