3,5-Dimethyl-1H-pyrrole-2-carbaldehyde → HCID 49823339, compound

HRID 1072178Notes

Reaction equation

HRID 1072178 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].[CH3:21][C:22]1[CH:26]=[C:25]([CH3:27])[NH:24][C:23]=1[CH:28]=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:28][C:23]4[NH:24][C:25]([CH3:27])=[CH:26][C:22]=4[CH3:21])[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 2704653,5-Dimethyl-1H-pyrrole-2-carbaldehydeHCID 223909724-((3-Chloro-4-fluorophenyl)amino)-7-methyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one

Product 1

HCID 49823339HCID 49823339, compoundYield 37%

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-dimethyl-1H-pyrrole-2-carbaldehyde (50 mg, 0.41 mmol) and piperidine (2 drops) in ethanol (3 mL) at 80° C. for 2 hours to give 50 mg (37%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 13.07 (br s, 1H, NH), 9.18 (s, 1H), 8.34 (s, 1H), 7.69 (m, 1H), 7.35 (s, 1H), 7.30-7.40 (m, 2H), 6.05 (s, 1H), 3.32 (s, 3H, CH3), 2.34 (s, 3H, CH3), 2.16 (s, 3H, CH3). MS 398 [M++1].

Sources & evidence

ORD record
ord-c00b8ab6508f4e2fb1be5fe55fb3f8a2
Source dataset
uspto-grants-2005_06
Patent number
US06908930B2

Reaction notes

Loading…