Water → 2,2-Dimethylpropionic acid 4-[3-(4-fluorophenyl)-1,9-dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]indol-6-yl]-thiazol-2-ylmethyl ester

HRID 559174Notes

Reaction equation

HRID 559174 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:28](=[O:29])[N:27]([CH3:30])[C:11]3[N:12]([CH3:26])[C:13]4[C:18]([C:10]=3[CH:9]=2)=[CH:17][C:16]([C:19]2[N:20]=[C:21]([CH2:24][OH:25])[S:22][CH:23]=2)=[CH:15][CH:14]=4)=[CH:4][CH:3]=1.[C:31](Cl)(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33].O>N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:28](=[O:29])[N:27]([CH3:30])[C:11]3[N:12]([CH3:26])[C:13]4[C:18]([C:10]=3[CH:9]=2)=[CH:17][C:16]([C:19]2[N:20]=[C:21]([CH2:24][O:25][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[S:22][CH:23]=2)=[CH:15][CH:14]=4)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 62493Pivaloyl chlorideHCID 669982663-(4-Fluorophenyl)-6-(2-hydroxymethylthiazol-4-yl)-1,9-dimethyl-1,9-dihydropyrido[2,3-b]indol-2-one

Product 1

HCID 669978782,2-Dimethylpropionic acid 4-[3-(4-fluorophenyl)-1,9-dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]indol-6-yl]-thiazol-2-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

200 mg (0.48 mmol) of compound 3-(4-fluorophenyl)-6-(2-hydroxymethylthiazol-4-yl)-1,9-dimethyl-1,9-dihydropyrido[2,3-b]indol-2-one from Example 63 are dissolved in 3 ml of pyridine. 294 μl (2.38 mmol) of pivaloyl chloride are added and the mixture is then stirred at ambient temperature for 2 hours. H2O is added, the mixture is extracted with EtOAc, the organic phase is washed with a saturated NH4Cl solution and then dried over MgSO4, and the product is filtered and concentrated. Purification is carried out by chromatography on a silica gel column, elution being carried out with EtOAc.

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. washthe organic phase is washed with a saturated NH4Cl solution
  3. dry with materialdried over MgSO4
  4. filtrationthe product is filtered
  5. concentrationconcentrated
  6. customPurification
  7. washis carried out by chromatography on a silica gel column, elution

Sources & evidence

ORD record
ord-d842bd165ed34c0cae959adb6443ebf8
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

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