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 2093923Notes

Reaction equation

HRID 2093923 reaction equation
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]

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8e2cd881b28b402ba68af5104531fe6d
Source dataset
uspto-grants-2013_05
Patent number
US08445501B2

Reaction notes

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