Pyridine-3-sulfonyl chloride hydrochloride → HCID 58477224, compound

HRID 876527Notes

Reaction equation

HRID 876527 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:3]=1.[NH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[O:21][C:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]([F:32])([F:31])[F:30])=[CH:19][C:18]2=[O:33]>N1C=CC=CC=1>[O:33]=[C:18]1[C:17]2[C:22](=[C:13]([NH:12][S:8]([C:4]3[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=3)(=[O:10])=[O:9])[CH:14]=[CH:15][CH:16]=2)[O:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]([F:32])([F:30])[F:31])=[CH:19]1

Participants

4

Reactant 2

HCID 12571517Pyridine-3-sulfonyl chloride hydrochlorideHCID 58477328HCID 58477328, compound

Product 1

HCID 58477224HCID 58477224, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

Pyridine-3-sulfonyl chloride hydrochloride 12 (280 mg, 1.3 mmol) was added to a solution of 8-amino-2-(2-(trifluoromethyl)phenyl)-4H-chromen-4-one 11 (100 mg, 0.328 mmol) in pyridine (5 mL). The reaction mixture was heated at 80° C. for 12 h. The pyridine was removed en vacuo. The residue was taken up in CH2Cl2, washed with sat. aq NaHCO3, dried (MgSO4) and concentrated. The crude residue was purified by MPLC eluting with CH2Cl2/MeOH (0-10%) followed by recrystallization from CH3CN to give Compound 326 (46 mg, 31% yield). MS (ESI) calcd for C21H13F3N2O4S: 446.1. found: 447 [M+H].

Workup

  1. customThe pyridine was removed en vacuo
  2. washwashed with sat. aq NaHCO3
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude residue was purified by MPLC
  6. washeluting with CH2Cl2/MeOH (0-10%)
  7. customfollowed by recrystallization from CH3CN

Sources & evidence

ORD record
ord-045ee6f27d454752972e1fcf763b8c78
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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