Dimethylsulphamoyl chloride → HCID 46913146, compound

HRID 1397858Notes

Reaction equation

HRID 1397858 reaction equation
[NH2:1][C:2]1[C:3]([F:22])=[C:4]([C:18]([F:21])=[CH:19][CH:20]=1)[C:5]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([C:16]#[N:17])[CH:14]=2)[NH:9][CH:8]=1)=[O:6].[CH3:23][N:24]([CH3:29])[S:25](Cl)(=[O:27])=[O:26]>N1C=CC=CC=1>[C:16]([C:13]1[CH:14]=[C:15]2[C:7]([C:5]([C:4]3[C:3]([F:22])=[C:2]([NH:1][S:25]([N:24]([CH3:29])[CH3:23])(=[O:27])=[O:26])[CH:20]=[CH:19][C:18]=3[F:21])=[O:6])=[CH:8][NH:9][C:10]2=[N:11][CH:12]=1)#[N:17]

Participants

4

Reactant 2

HCID 83372Dimethylsulphamoyl chlorideHCID 66647207HCID 66647207, compound

Product 1

HCID 46913146HCID 46913146, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 3-(3-amino-2,6-difluoro-benzoyl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (28, 50.0 mg, 0.168 mmol), 0.50 mL of pyridine was added, followed by addition of N,N-dimethylamino-sulfonyl chloride (32, 54 μL, 0.51 mmol) and the solution was stirred at room temperature for 2 days. The reaction mixture was extracted with 1 M aqueous hydrochloric acid and with ethyl acetate. The organic layer was washed with water, then brine, dried over magnesium sulfate, filtered, and the filtrate was concentrated under vacuum. The crude material was purified by silica gel column chromatography eluting with ethyl acetate and hexane. Appropriate fractions were combined and the solvent removed under reduced pressure to provide the desired compound (P-0007, 28 mg). MS(ESI)[M+H+]+=405.8.

Workup

  1. extractionThe reaction mixture was extracted with 1 M aqueous hydrochloric acid and with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialbrine, dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe crude material was purified by silica gel column chromatography
  7. washeluting with ethyl acetate and hexane
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-56ae502b765d4e4f94995121041fb320
Source dataset
uspto-grants-2014_12
Patent number
US08901301B2

Reaction notes

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