2-Fluorobenzenesulphonyl chloride → N-[4-(4-Amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-6-methyl-pyridin-2-yl]-2-fluoro-benzenesulfonamide

HRID 736346Notes

Reaction equation

HRID 736346 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]([CH3:30])[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]=[C:28]([CH3:30])[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 68906511N-[4-(4-Amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-6-methyl-pyridin-2-yl]-2-fluoro-benzenesulfonamideYield 62.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Fluoro-benzenesulfonyl chloride (68.9 mg, 035 mmol) was added to a solution of (4-Amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(2-amino-6-methyl-pyridin-4-yl)-methanone (100 mg, 0.32 mmol) in pyridine (2 mL). The mixture was stirred for 2 h at room temperature. The reaction mixture was quenched with H2O (2 mL) and concentrated in vacuo. The resulting residue was triturated with MeOH, filtered, and dried. Purification by flash column chromatography [ethyl acetate/hexanes 3:7—(20% NH4OH/MeOH)/ethyl acetate/hexanes 5:65:30] afforded the title compound as a yellow oil (94 mg, 62%). MS: 469.3 (MH+); HPLC Rf: 4.46 min. (HPLC method 4).

Workup

  1. customThe reaction mixture was quenched with H2O (2 mL)
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was triturated with MeOH
  4. filtrationfiltered
  5. customdried
  6. customPurification by flash column chromatography [ethyl acetate/hexanes 3:7—(20% NH4OH/MeOH)/ethyl acetate/hexanes 5:65:30]

Sources & evidence

ORD record
ord-c4abf53601114c77a2f4c6e502de96bc
Source dataset
uspto-grants-2009_09
Patent number
US07595325B2

Reaction notes

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