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

HRID 1171769ノート

反応式

HRID 1171769 の反応式
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

参加物

6

反応物 4

HCID 313Hydrochloric Acid2 回HCID 85320Ethyl isothiocyanatoformateHCID 5360545SodiumHCID 670684721-Boc-4-[(2-Ethoxycarbonyl-1H-pyrrol-3-ylamino)methyl]piperidine

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0a03177471144ba0b9066592a6f78b9e
出典データセット
uspto-grants-2010_11
特許番号
US07829707B2

反応ノート

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