Methanol → 4-(5-Cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-propionyl-piperidin-4-yl)-amide

HRID 2093923노트

반응식

HRID 2093923 반응식
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]([C:11]2[C:15]3[N:16]=[CH:17][N:18]=[C:19]([C:20]4[C:28]5[O:27][CH2:26][O:25][C:24]=5[CH:23]=[CH:22][C:21]=4[O:29][CH2:30][CH:31]4[CH2:33][CH2:32]4)[C:14]=3[NH:13][CH:12]=2)=[O:10])[CH2:4][CH2:3]1.C1CCN2C(=NCCC2)CC1.[C:45](Cl)(=[O:48])[CH2:46][CH3:47].CO>ClCCl>[C:45]([N:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]([C:11]2[C:15]3[N:16]=[CH:17][N:18]=[C:19]([C:20]4[C:28]5[O:27][CH2:26][O:25][C:24]=5[CH:23]=[CH:22][C:21]=4[O:29][CH2:30][CH:31]4[CH2:32][CH2:33]4)[C:14]=3[NH:13][CH:12]=2)=[O:10])[CH2:4][CH2:3]1)(=[O:48])[CH2:46][CH3:47]

참가 물질

6

반응물 4

HCID 887MethanolHCID 62324Propionyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 668666464-(5-Cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide hydrochloride

생성물 1

HCID 442058374-(5-Cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-propionyl-piperidin-4-yl)-amide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

4-(5-Cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide hydrochloride from example A138 (472 mg; 1.0 mmol) and DBU (2.5 mmol) is dissolved in dry dichloromethane (5 mL). Propionyl chloride (1.1 mmol) is syringed into the reaction mixture at ice bath temperature. After complete addition stirring is continued at ambient temperature over night. Methanol (1 mL) is added and stirring is continued for two hours. The volatiles are evaporated. The residue is purified by reversed phase preparative HPLC. The collected product fraction is freeze-dried to yield 375 mg of the title compound as colorless solid.

후처리

  1. additionAfter complete addition
  2. waitis continued at ambient temperature over night
  3. stirringstirring
  4. customThe volatiles are evaporated
  5. customThe residue is purified by reversed phase preparative HPLC
  6. customThe collected product fraction is freeze-dried

출처 및 근거

ORD 기록
ord-8e2cd881b28b402ba68af5104531fe6d
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445501B2

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