2-Propanesulfonyl chloride → HCID 56966001, compound

HRID 1036929Notes

Reaction equation

HRID 1036929 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:17][C:16]([CH3:19])([CH3:18])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:20]#[N:21])[CH:14]=2)[NH:9]1.[CH3:22][CH:23]([S:25](Cl)(=[O:27])=[O:26])[CH3:24]>N1C=CC=CC=1.O>[C:20]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][S:25]([CH:23]([CH3:24])[CH3:22])(=[O:27])=[O:26])[CH2:17][C:16]2([CH3:18])[CH3:19])#[N:21]

Participants

5

Reactant 2

HCID 824082-Propanesulfonyl chlorideHCID 67290159HCID 67290159, compound

Product 1

HCID 56966001HCID 56966001, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of 2-(2-aminophenyl)-4,4-dimethyl-1,2,3,4-tetrahydroquinoline-6-carbonitrile (500 mg, 1.8 mmol) in pyridine (3 mL) was added propane-2-sulfonyl chloride (201 μL, 1.8 mmol) at ice-bath under nitrogen. After addition, the resulting mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with water, and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, concentrated. The residue was purified by HPLC to give propane-2-sulfonic acid [2-(6-cyano-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-amide LC/MS m/e obsd. (ESI+) [(M+H)+] 384.3.

Workup

  1. additionAfter addition
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-4d4280235b8d4c2e8b8a684da2653c98
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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