Methyl 3-amino-4-chloro-2-((3-hydroxypropyl)amino]benzoate → Methyl 4-chloro-2-[(3-hydroxypropyl)amino]-3-({[6-methoxy-2-(trifluoromethyl)pyridin-3-yl]carbamothioyl}amino)benzoate

HRID 1628596Notes

Reaction equation

HRID 1628596 reaction equation
[NH2:1][C:2]1[C:3]([NH:13][CH2:14][CH2:15][CH2:16][OH:17])=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[C:5]([O:7][CH3:8])=[O:6].[N:18]([C:21]1[C:22]([C:29]([F:32])([F:31])[F:30])=[N:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)=[C:19]=[S:20]>O1CCCC1>[Cl:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([NH:13][CH2:14][CH2:15][CH2:16][OH:17])[C:2]=1[NH:1][C:19](=[S:20])[NH:18][C:21]1[C:22]([C:29]([F:32])([F:30])[F:31])=[N:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 68739849Methyl 3-amino-4-chloro-2-((3-hydroxypropyl)amino]benzoateHCID 866329283-Isothiocyanato-6-methoxy-2-(trifluoromethyl)pyridine

Product 1

HCID 86632929Methyl 4-chloro-2-[(3-hydroxypropyl)amino]-3-({[6-methoxy-2-(trifluoromethyl)pyridin-3-yl]carbamothioyl}amino)benzoateYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-amino-4-chloro-2-[(3-hydroxypropyl)amino]benzoate (1.00 g, 3.87 mmol) and 3-isothiocyanato-6-methoxy-2-(trifluoromethyl)pyridine (1.81 g, 7.73 mmol) in tetrahydrofuran (10 mL) was stirred at room temperature for 3 days. The reaction mixture was concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 30-100% ethyl acetate/n-hexane gradient mixture to give the title compound (1.85 g, 3.75 mmol, 97%) as a pale red amorphous.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by flash chromatography on silica gel eluting with a 30-100% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-091607f1f9ce4c34957c47ec2c648414
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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