2-Fluorobenzenesulphonyl chloride → HCID 68906522, compound

HRID 736357Notes

Reaction equation

HRID 736357 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].[NH2:12][C:13]1[C:14]2[C:21]([C:22]([C:24]3[CH:29]=[C:28]([O:30][CH3:31])[N:27]=[C:26]([NH2:32])[CH:25]=3)=[O:23])=[CH:20][N:19]([CH:33]([CH3:35])[CH3:34])[C:15]=2[N:16]=[CH:17][N:18]=1>N1C=CC=CC=1>[NH2:12][C:13]1[C:14]2[C:21]([C:22]([C:24]3[CH:29]=[C:28]([O:30][CH3:31])[N:27]=[C:26]([NH:32][S:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])(=[O:10])=[O:9])[CH:25]=3)=[O:23])=[CH:20][N:19]([CH:33]([CH3:35])[CH3:34])[C:15]=2[N:16]=[CH:17][N:18]=1

Participants

4

Reactant 2

HCID 1377612-Fluorobenzenesulphonyl chlorideHCID 68904398HCID 68904398, compound

Product 1

HCID 68906522HCID 68906522, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Fluoro-benzenesulfonyl chloride (0.05 mL, 0.37 mmol) was added to a solution of (4-Amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(2-amino-6-methoxy-pyridin-4-yl)-methanone (100 mg, 0.31 mmol) in pyridine (2 mL) and stirred for 2 h at room temperature. The reaction mixture was quenched with H2O (100 mL) and extracted with hot EtOAC/MeOH (95:5 3×100 mL). The combined organic extracts were cooled to room temperature and the solid was filtered and dried to provide the title compound as a white solid (69 mg, 47%). MS: 485.3 (MH+); HPLC Rf: 2.7 min. (HPLC method 2); HPLC purity: 100%.

Workup

  1. customThe reaction mixture was quenched with H2O (100 mL)
  2. extractionextracted with hot EtOAC/MeOH (95:5 3×100 mL)
  3. temperatureThe combined organic extracts were cooled to room temperature
  4. filtrationthe solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-2c81220fce484a70aeab1bacb8006ffd
Source dataset
uspto-grants-2009_09
Patent number
US07595325B2

Reaction notes

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