4-(3-Chloro 4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one → HCID 69799072, compound

HRID 1072193Notes

Reaction equation

HRID 1072193 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])[NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8].[CH:20]([C:22]1[NH:26][C:25]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:24][C:23]=1[CH3:32])=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:20][C:22]4[NH:26][C:25]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:24][C:23]=4[CH3:32])[C:17](=[O:19])[NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 98787694-(3-Chloro 4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-oneHCID 223909933-(5-Formyl-4-methyl-1H-pyrrol-2-yl)propanoic acid

Product 1

HCID 69799072HCID 69799072, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(3-chloro-4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (70 mg, 0.25 mmol), 3-(5-formyl-4-methyl-1H-pyrrol-2-yl)-propionic acid (54.4 mg, 0.3 mmol) and piperidine (3 drops) in ethanol (2 mL) was stirred at room temperature for 4 days. The reaction was concentrated, the residue was dissolved in water and acidified with 1N HCl to pH=2. The resultant solid was then washed with water, ethanol and dried to give 93.9 mg (85%) of the title compound. 1H NMR (360 MHz, DMSO-d6) δ 13.18 (br s, 1H, NH), 12.19 (br s, 1H, COOH), 11.61 (br s, 1H, NH), 9.09 (s, 1H), 8.27 (s, 1H), 7.70 (m, 1H), 7.39 (m, 1H), 7.30-7.35 (m, 2H), 6.07 (s, 1H), 2.90 (t, J=7.2 Hz, 2H, CH2), 2.60 (t, J=7.2 Hz, 2H, CH2), 2.16 (s, 3H, CH3). MS 442 [M++1].

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthe residue was dissolved in water
  3. washThe resultant solid was then washed with water, ethanol
  4. customdried

Sources & evidence

ORD record
ord-593694a1c14d42ebaec0f0e864b68b2f
Source dataset
uspto-grants-2005_06
Patent number
US06908930B2

Reaction notes

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