Water → HCID 16226476, compound

HRID 559202Notes

Reaction equation

HRID 559202 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:28](=[O:29])[N:27]([CH3:30])[C:12]2[N:13]([CH3:26])[C:14]3[C:19]([C:11]=2[CH:10]=1)=[CH:18][C:17]([C:20]1[NH:21][N:22]=[CH:23][C:24]=1[CH3:25])=[CH:16][CH:15]=3.[C:31](Cl)(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33].O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:28](=[O:29])[N:27]([CH3:30])[C:12]2[N:13]([CH3:26])[C:14]3[C:19]([C:11]=2[CH:10]=1)=[CH:18][C:17]([C:20]1[C:24]([CH3:25])=[CH:23][N:22]([C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[N:21]=1)=[CH:16][CH:15]=3

Participants

5

Reactant 3

HCID 962WaterHCID 62493Pivaloyl chlorideHCID 66997918HCID 66997918, compound2×

Product 1

HCID 16226476HCID 16226476, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.14 g (0.32 mmol) of compound from Example 53, 3-(2,4-dichlorophenyl)-1,9-dimethyl-6-(4-methyl-2H-pyrazol-3-yl)-1,9-dihydropyrido[2,3-b]indol-2-one is dissolved in 5 ml of pyridine. 0.2 ml (1.6 mmol) of pivaloyl chloride is added. The mixture is stirred at ambient temperature for 2 hours. The reaction medium is poured into water, and extracted with EtOAc. Washing with a saturated NaCl solution, drying over Na2SO4 and then adsorbing onto silica are performed. Purification is carried out by chromatography on a silica column, elution being carried out with a 75/25 EtOAc/cyclohexane mixture and then with pure EtOAc.

Workup

  1. extractionextracted with EtOAc
  2. washWashing with a saturated NaCl solution
  3. dry with materialdrying over Na2SO4
  4. customPurification
  5. washis carried out by chromatography on a silica column, elution

Sources & evidence

ORD record
ord-b422e59b089645e7a7c4f63e451d75ce
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

Loading…