3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)propanoic Acid → 3-{5-[4-(3-Chloro-4-fluoro-phenylamino)-7-methyl-6-oxo-6,7-dihydro-pyrrolo [2,3-D]pyrimidin-5-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-YL}-propionic acid

HRID 397420Notes

Reaction equation

HRID 397420 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].[CH:21]([C:23]1[NH:27][C:26]([CH3:28])=[C:25]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])[C:24]=1[CH3:34])=O>N1CCCCC1.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[C:18](=[CH:21][C:23]4[NH:27][C:26]([CH3:28])=[C:25]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])[C:24]=4[CH3:34])[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]

Participants

5

Reactant 2

HCID 15125203-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)propanoic AcidHCID 223909724-((3-Chloro-4-fluorophenyl)amino)-7-methyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one

Product 1

HCID 697973523-{5-[4-(3-Chloro-4-fluoro-phenylamino)-7-methyl-6-oxo-6,7-dihydro-pyrrolo [2,3-D]pyrimidin-5-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-YL}-propionic acidYield 23%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

4-(3-Chloro-4-fluoro-phenylamino)-7-methyl-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (100 mg, 0.34 mmol) was condensed with 3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)-propionic acid (80 mg, 0.41 mmol) and piperidine (2 drops) in ethanol (3 mL) at 80° C. for 2 hours to give 36 mg (23%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 13.15 (br s, 1H, NH), 12.07 (br s, 1H, COOH), 9.18 (s, 1H), 8.33 (s, 1H), 7.71 (m, 1H), 7.40 (s, 1H), 7.30-7.39 (m, 2H), 3.32 (s, 3H, CH3), 2.63 (m, 2H, CH), 2.35 (m, 2H, CH2), 2.33 (s, 3H, CH3), 2.13 (s, 3H, CH3).

Sources & evidence

ORD record
ord-71ac3086bd474daf844259544cd527ab
Source dataset
uspto-grants-2003_08
Patent number
US06610688B2

Reaction notes

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