5-formyl-4-methyl-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amide → 5-[4-(3-Chloro-4-fluoro-phenylamino)-7-methyl-6-oxo-6,7-dihydro-pyrrolo [2,3-D]pyrimidin-5-ylidenemethyl]-4-methyl-1H-pyrrole-2-carboxylic acid (2-morpholin-4-YL-ethyl)-amide

HRID 1072168Notes

Reaction equation

HRID 1072168 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[CH2:18][C:17](=[O:19])[N:16]([CH3:20])[C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8].[N:21]1([CH2:27][CH2:28][NH:29][C:30]([C:32]2[NH:33][C:34]([CH:38]=O)=[C:35]([CH3:37])[CH:36]=2)=[O:31])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>N1CCCCC1.C(O)C.CN(C=O)C.O>[N:21]1([CH2:27][CH2:28][NH:29][C:30]([C:32]2[NH:33][C:34]([CH:38]=[C:18]3[C:11]4[C:10]([NH:9][C:4]5[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=5)=[N:15][CH:14]=[N:13][C:12]=4[N:16]([CH3:20])[C:17]3=[O:19])=[C:35]([CH3:37])[CH:36]=2)=[O:31])[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1

Participants

7

Reactant 2

HCID 112770865-formyl-4-methyl-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amideHCID 223909724-((3-Chloro-4-fluorophenyl)amino)-7-methyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one

Product 1

HCID 498233465-[4-(3-Chloro-4-fluoro-phenylamino)-7-methyl-6-oxo-6,7-dihydro-pyrrolo [2,3-D]pyrimidin-5-ylidenemethyl]-4-methyl-1H-pyrrole-2-carboxylic acid (2-morpholin-4-YL-ethyl)-amideYield 31%

Reagents, catalysts & solvents 4

HCID 8082PiperidineCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(3-chloro-4-fluoro-phenylamino)-7-methyl-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (244 mg, 0.83 mmol), 5-formyl-4-methyl-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amide (1.2 equiv.) and piperidine (1 drop) in ethanol and DMF (2 mL) was stirred at 90° C. for 2 hours. The reaction was diluted with water and the precipitate was collected by vacuum filtration, washed with water, ethyl acetate and hexane and dried to give 138.5 mg (31%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 13.39 (br s, 1H, NH), 9.29 (br s, 1H), 8.38 (m, 2H), 7.72 (m 1H), 7.39 (s, 1H, H-vinyl), 7.34 (m, 2H), 6.81 (s, 1H), 3.56 (m, 4H, 2×CH2), 3.35 (m, 2H, CH2), 3.31 (s, 3H, CH3), 2.45 (m, 2H, CH2), 2.41 (m, 4H, 2×CH2), 2.20 (s, 3H, CH3). MS 540 [M+1].

Workup

  1. filtrationthe precipitate was collected by vacuum filtration
  2. washwashed with water, ethyl acetate and hexane
  3. customdried

Sources & evidence

ORD record
ord-9cf3cdf2a6f2441e99687af90af82895
Source dataset
uspto-grants-2005_06
Patent number
US06908930B2

Reaction notes

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