Dichloromethane → HCID 10217697, compound

HRID 2416212Notes

Reaction equation

HRID 2416212 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[S:12][CH:13]=[C:14]([C:16]3[C:17](=[O:29])[NH:18][C:19]4[C:24]([CH:25]=3)=[CH:23][CH:22]=[C:21]([C:26](O)=[O:27])[CH:20]=4)[N:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)Cl.C(Cl)(=O)C(C)(C)C.[NH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1>O>[C:1]1([S:7]([CH2:10][C:11]2[S:12][CH:13]=[C:14]([C:16]3[C:17](=[O:29])[NH:18][C:19]4[C:24]([CH:25]=3)=[CH:23][CH:22]=[C:21]([C:26]([N:40]3[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]3)=[O:27])[CH:20]=4)[N:15]=2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8082PiperidineHCID 62493Pivaloyl chlorideHCID 22638593HCID 22638593, compound

Product 1

HCID 10217697HCID 10217697, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 3-(2-benzenesulfonylmethyl-thiazol-4-yl)-1H-quinolin-2-one-7-carboxylic acid (Example 8733 step (h), 0.1 g, 0.2 mmol) and 5 mL of anhydrous CH2Cl2 was added TEA (0.2 mL, 1.4 mmol) and pivaloyl chloride (0.1 mL, 0.8 mmol). The solution was stirred overnight at RT. The reaction was now homogenous and piperidine (0.5 mL, 5.1 mmol) was added. After 6 h, the reaction was diluted with H2O. The aqueous solution was extracted with EtOAc (6×). The combined EtOAc layers were washed with brine, dried over MgSO4, and concentrated in vacuo. The solid was suspended in a minimum of EtOAc and filtered to give a solid. MS m/z: 494.1 (M+1). Anal. Calc'd for C25H23N3O4S2.0.5H2O: C, 59.74; H, 4.81; N, 8.36. Found: C, 59.64; H, 4.82; N, 8.30.

Workup

  1. waitAfter 6 h
  2. extractionThe aqueous solution was extracted with EtOAc (6×)
  3. washThe combined EtOAc layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. filtrationfiltered
  7. customto give a solid

Sources & evidence

ORD record
ord-04803e4d088f46e2af59bccb5f8c8066
Source dataset
uspto-grants-2004_11
Patent number
US06822097B1

Reaction notes

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