Water → HCID 66997963, compound

HRID 559181Notes

Reaction equation

HRID 559181 reaction equation
C(OC(=O)[NH:10][CH2:11][C:12]1[S:13][CH:14]=[C:15]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([CH3:26])[C:21]2[N:27]([CH3:39])[C:28](=[O:38])[C:29]([C:31]4[CH:36]=[CH:35][C:34]([Br:37])=[CH:33][CH:32]=4)=[CH:30][C:20]3=2)[N:16]=1)C1C=CC=CC=1.C1(SC)C=CC=CC=1.O>C(O)(C(F)(F)F)=O>[NH2:10][CH2:11][C:12]1[S:13][CH:14]=[C:15]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([CH3:26])[C:21]2[N:27]([CH3:39])[C:28](=[O:38])[C:29]([C:31]4[CH:36]=[CH:35][C:34]([Br:37])=[CH:33][CH:32]=4)=[CH:30][C:20]3=2)[N:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7520ThioanisoleHCID 66998381HCID 66998381, compound

Product 1

HCID 66997963HCID 66997963, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of compound A {4-[3-(4-bromophenyl)-1,9-dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]indol-6-yl]thiazol-2-ylmethyl}carbamic acid benzyl ester (200 mg, 0.32 mmol) and thioanisole (308 μl, 2.60 mmol) in 2 ml of TFA is left to stir overnight at ambient temperature. H2O is added, the mixture is extracted with EtOAc, the organic phases are washed with H2O and the product is dried over MgSO4, filtered and concentrated. Purification is carried out by chromatography on a silica column, elution being carried out with 100% EtOAc and then with an EtOAc/5% MeOH mixture then with an EtOAc/5% MeOH/1% TEA mixture. The residue is taken up in a 1/1 EtOAc/Et2O mixture and the product is filtered and washed with a minimum amount of Et2O.

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. washthe organic phases are washed with H2O
  3. dry with materialthe product is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. washis carried out by chromatography on a silica column, elution
  8. filtrationthe product is filtered
  9. washwashed with a minimum amount of Et2O

Sources & evidence

ORD record
ord-9efbb39086024a319d1ca8e300d2c69e
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

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