Thioanisole → 6-(2-Aminomethylthiazol-4-yl)-3-(2,4-dichlorophenyl)-1,9-dimethyl-1,9-dihydropyrido[2,3-b]indol-2-one

HRID 559250Notes

Reaction equation

HRID 559250 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]([CH3:40])[C:28](=[O:39])[C:29]([C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=4[Cl:38])=[CH:30][C:20]3=2)[N:16]=1)C1C=CC=CC=1.C1(SC)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>FC(F)(F)C(O)=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]([CH3:40])[C:28](=[O:39])[C:29]([C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=4[Cl:38])=[CH:30][C:20]3=2)[N:16]=1

Participants

5

Reactant 3

HCID 7520ThioanisoleHCID 11430Potassium CarbonateHCID 66998447{4-[3-(2,4-dichlorophenyl)-1,9-dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]indol-6-yl]thiazol-2-ylmethyl}carbamic acid benzyl ester

Product 1

HCID 669981646-(2-Aminomethylthiazol-4-yl)-3-(2,4-dichlorophenyl)-1,9-dimethyl-1,9-dihydropyrido[2,3-b]indol-2-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

780 mg (1.3 mmol) of compound A {4-[3-(2,4-dichlorophenyl)-1,9-dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]indol-6-yl]thiazol-2-ylmethyl}carbamic acid benzyl ester are dissolved in 12 ml of trifluoroacetic acid. 8 ml (10.3 mmol) of thioanisole are added and the mixture is stirred at ambient temperature for 16 hours. It is poured into a saturated K2CO3 solution and the mixture is extracted with EtOAc. The organic phase is adsorbed onto silica and purification is carried out on a silica column, elution being carried out with EtOAc and then with 90/10/1 EtOAc/MeOH/NH3.

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. customThe organic phase is adsorbed onto silica and purification
  3. washis carried out on a silica column, elution

Sources & evidence

ORD record
ord-cbf6eee3d0f34932948fc124c28b74c5
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

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