2-Fluorobenzenesulphonyl chloride → N-[4-(4-Amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-pyridin-2-yl]-2-fluoro-benzenesulfonamide

HRID 736349Notes

Reaction equation

HRID 736349 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](C)[N:27]=[C:26]([NH2:31])[CH:25]=3)=[O:23])=[CH:20][N:19]([CH:32]([CH3:34])[CH3:33])[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]=[CH:28][N:27]=[C:26]([NH:31][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:32]([CH3:34])[CH3:33])[C:15]=2[N:16]=[CH:17][N:18]=1

Participants

4

Reactant 2

HCID 1377612-Fluorobenzenesulphonyl chlorideHCID 68902711(4-Amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(2-amino-6-methyl-pyridin-4-yl)-methanone

Product 1

HCID 68902763N-[4-(4-Amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-pyridin-2-yl]-2-fluoro-benzenesulfonamideYield 30%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

2-Fluoro-benzenesulfonyl chloride (0.11 mL, 0.81 mmol) was added to a solution of (4-Amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(2-amino-6-methyl-pyridin4-yl)-methanone (200 mg, 0.67 mmol) in pyridine (2 mL). The mixture was stirred for 2 h at 80° C. The reaction mixture was quenched with H2O (10 mL) and extracted with hot EtOAC/MeOH (95:5, 3×10 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash column chromatography (ethyl acetate/MeOH 99:1) afforded the title compound as a yellow solid (91 mg, 30%). MS: 455.8 (MH+); HPLC Rf: 5.98 min. (HPLC method 4); HPLC purity: 100%.

Workup

  1. customThe reaction mixture was quenched with H2O (10 mL)
  2. extractionextracted with hot EtOAC/MeOH (95:5, 3×10 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography (ethyl acetate/MeOH 99:1)

Sources & evidence

ORD record
ord-7bf6b882c8b840479339dba4076fd018
Source dataset
uspto-grants-2009_09
Patent number
US07595325B2

Reaction notes

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