2,6-Difluorophenyl isocyanate → 1-[3-(4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-ylsulfanyl)-phenyl]-3-(2,6-difluoro-phenyl)-urea

HRID 916775Notes

Reaction equation

HRID 916775 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[C:17]3[C:16]([NH2:18])=[N:15][CH:14]=[N:13][C:12]=3[N:11]([CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[F:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:26]=1[N:32]=[C:33]=[O:34]>N1C=CC=CC=1>[NH2:18][C:16]1[C:17]2[C:9]([S:8][C:4]3[CH:3]=[C:2]([NH:1][C:33]([NH:32][C:26]4[C:27]([F:31])=[CH:28][CH:29]=[CH:30][C:25]=4[F:24])=[O:34])[CH:7]=[CH:6][CH:5]=3)=[CH:10][N:11]([CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[C:12]=2[N:13]=[CH:14][N:15]=1

Participants

4

Reactant 2

HCID 5221622,6-Difluorophenyl isocyanateHCID 672191925-(3-Amino-phenylsulfanyl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Product 1

HCID 672193031-[3-(4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-ylsulfanyl)-phenyl]-3-(2,6-difluoro-phenyl)-ureaYield 41%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a round-bottom flask with pyridine (3 mL) was added 5-(3-Amino-phenylsulfanyl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (16.3 mg, 0.05 mmole) and 1,3-Difluoro-2-isocyanato-benzene (15.5 mg, 0.1 mmole). The reaction mixture was stirred at room temperature overnight and extracted with EtOAc (40 mL) and water (40 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated. Purification through flash column (methylene chloride/methanol: 96/4) gave the title compound as a light yellow solid (9.8 mg, 41%). MS: 481.1 (MH+); HPLC Rf: 7.559 min.; HPLC purity: 96%.

Workup

  1. extractionextracted with EtOAc (40 mL) and water (40 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customPurification through flash column (methylene chloride/methanol: 96/4)

Sources & evidence

ORD record
ord-2de6e5b7f2ce4085980fd8c560a56d33
Source dataset
uspto-grants-2007_09
Patent number
US07271262B2

Reaction notes

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