Piperidine → 5-(6-Oxo-4-piperidin-1-YL-6,7-dihydro-pyrrolo[2,3-D]pyrimidin-5-ylidenemethyl)-1H-pyrrole-2-carboxylic acid (2-morpholin-4-YL-ethyl)-amide

HRID 1072137Notes

Reaction equation

HRID 1072137 reaction equation
Cl[C:2]1[C:3]2[CH2:10][C:9](=[O:11])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[N:12]1([CH2:18][CH2:19][NH:20][C:21]([C:23]2[NH:24][C:25]([CH:28]=O)=[CH:26][CH:27]=2)=[O:22])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.[NH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>C(O)C>[N:12]1([CH2:18][CH2:19][NH:20][C:21]([C:23]2[NH:24][C:25]([CH:28]=[C:10]3[C:3]4[C:2]([N:30]5[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]5)=[N:7][CH:6]=[N:5][C:4]=4[NH:8][C:9]3=[O:11])=[CH:26][CH:27]=2)=[O:22])[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 120958704-chloro-5H,6H,7H-pyrrolo[2,3-d]pyrimidin-6-oneHCID 120958715-formyl-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amide

Product 1

HCID 865914095-(6-Oxo-4-piperidin-1-YL-6,7-dihydro-pyrrolo[2,3-D]pyrimidin-5-ylidenemethyl)-1H-pyrrole-2-carboxylic acid (2-morpholin-4-YL-ethyl)-amideYield 50.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 4-chloro-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (85 mg, 0.5 mmol) and 5-formyl-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amide (125 mg, 0.5 mmol) in ethanol (4 mL) was added 0.2 mL of piperidine. The mixture was stirred at room temperature for 20 hours. The yellow precipitate was filtered after cooled with an ice bath, washed with cold ethanol and dried to give 114 mg (50.6%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 13.23 (br s, 1H, NH), 11.68 (br s, 1H, NH), 8.39 (m, 1H, CONHCH2), 8.32 (s, 1H, H-vinyl), 7.11 (s, 1H), 6.91-6.98 (m, 2H), 3.56 (m, 4H, 2×CH2), 3.38 (m, 6H, 3×CH), 2.39-2.47 (m, 6H, 3×CH2), 1.65 (m, 6H, 3×CH2). MS 452.2 [M++1].

Workup

  1. filtrationThe yellow precipitate was filtered
  2. temperatureafter cooled with an ice bath
  3. washwashed with cold ethanol
  4. customdried

Sources & evidence

ORD record
ord-ae5e2dea50574d0ebbee8bf22ff330ad
Source dataset
uspto-grants-2005_06
Patent number
US06908930B2

Reaction notes

Loading…