4-(3-Chloro 4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one → HCID 69794807, compound

HRID 397406Notes

Reaction equation

HRID 397406 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:23][C:24]([CH:32]([CH3:34])[CH3:33])=[CH:25][C:26]=1[CH2:27][CH2:28][C:29]([OH:31])=[O:30])=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:23][C:24]([CH:32]([CH3:34])[CH3:33])=[CH:25][C:26]=4[CH2:27][CH2:28][C:29]([OH:31])=[O:30])[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 22390961HCID 22390961, compound

Product 1

HCID 69794807HCID 69794807, compoundYield 71%

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-(2-formyl-5-isopropyl-1H-pyrrol-3-yl)-propionic acid (54.4 mg, 0.26 mmol) and piperidine (3 drops) in ethanol (2 mL) was stirred at room temperature for 2 days. The precipitate was collected by vacuum filtration, washed with water, 1N HCl, water and finally ethanol, dried in vacuum oven to give 83 mg (71%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 13.44 (br s, 1H, NH), 12.15 (br s, 1H, COOH), 11.69 (br s, 1H, NH), 9.02 (br s, 1H), 8.29 (s, 1H), 7.77 (dd, J=2.5 & 6.4 Hz, 1H), 7.47 (s, 1H), 7.43 (m, 1H), 7.33 (t, J=8.9 Hz, 1H), 6.14 (d, J=2 Hz, 1H), 3.01 (m, 1H, CH(CH3)2), 2.83 (t, J=7.2 Hz, 2H, CH2), 2.48 (m, 2H, CH2), 1.21.27 (d, J=6.8 Hz, 6H, CH(CH3)2). MS 469 [M++1].

Workup

  1. filtrationThe precipitate was collected by vacuum filtration
  2. washwashed with water, 1N HCl, water and finally ethanol
  3. customdried in vacuum oven

Sources & evidence

ORD record
ord-36f19bda9f91496cac2d6563c3cc38fd
Source dataset
uspto-grants-2003_08
Patent number
US06610688B2

Reaction notes

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