Chlorosulfonyl isocyanate → HCID 66730841, compound

HRID 1028030Notes

Reaction equation

HRID 1028030 reaction equation
[CH2:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]3[N:17]=[CH:16][C:15]([S:18]([NH:21][C@@H:22]([CH3:27])[C:23]([F:26])([F:25])[F:24])(=[O:20])=[O:19])=[CH:14][CH:13]=3)[NH:9]2)=[CH:5][C:4]=1[F:28])[CH3:2].ClS([N:33]=[C:34]=O)(=O)=O>CN(C=O)C.C(#N)C>[C:34]([C:7]1[C:6]2[C:10](=[CH:11][C:3]([CH2:1][CH3:2])=[C:4]([F:28])[CH:5]=2)[NH:9][C:8]=1[C:12]1[N:17]=[CH:16][C:15]([S:18]([NH:21][C@@H:22]([CH3:27])[C:23]([F:25])([F:26])[F:24])(=[O:19])=[O:20])=[CH:14][CH:13]=1)#[N:33]

Participants

5

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 66730861HCID 66730861, compound

Product 1

HCID 66730841HCID 66730841, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-6-(6-ethyl-5-fluoro-1H-indol-2-yl)-N-(1,1,1-trifluoropropan-2-yl)pyridine-3-sulfonamide (0.22 g, 0.53 mmol) in a mixture of DMF (0.5 mL) and acetonitrile (0.5 mL) was added chlorosulfonyl isocyanate dropwise at −50° C. The reaction mixture was kept stirring at 0° C. for 0.5 hr and then quenched with ice, following by pouring into water. After 0.5 hr stirring at room temperature, the resulting solid was collected by filtration and washed with water, hexane and CH2Cl2. After air drying, (S)-6-(3-cyano-6-ethyl-5-fluoro-1H-indol-2-yl)-N-(1,1,1-trifluoropropan-2-yl)pyridine-3-sulfonamide was obtained and used in the next step without further purification.

Workup

  1. customquenched with ice
  2. additionby pouring into water
  3. stirringAfter 0.5 hr stirring at room temperature
  4. filtrationthe resulting solid was collected by filtration
  5. washwashed with water, hexane and CH2Cl2
  6. customAfter air drying

Sources & evidence

ORD record
ord-f9946d89fb3c4a28a506004b043a5747
Source dataset
uspto-grants-2014_05
Patent number
US08735414B2

Reaction notes

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