Methyl 3-amino-4-chloro-2-((3-hydroxypropyl)amino]benzoate → HCID 86632890, compound

HRID 1628497Notes

Reaction equation

HRID 1628497 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].[CH2:18]([C:20]1[C:25]([N:26]=[C:27]=[S:28])=[C:24]([CH2:29][CH3:30])[N:23]=[C:22]([CH3:31])[N:21]=1)[CH3:19]>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:27](=[S:28])[NH:26][C:25]1[C:24]([CH2:29][CH3:30])=[N:23][C:22]([CH3:31])=[N:21][C:20]=1[CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 68739849Methyl 3-amino-4-chloro-2-((3-hydroxypropyl)amino]benzoateHCID 86632891HCID 86632891, compound

Product 1

HCID 86632890HCID 86632890, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of methyl 3-amino-4-chloro-2-[(3-hydroxypropyl)amino]benzoate (3.30 g, 12.8 mmol) and 4,6-diethyl-5-isothiocyanato-2-methylpyrimidine (5.28 g, 25.5 mmol) in tetrahydrofuran (25 mL) was stirred at 65° C. for 3 days. The mixture was concentrated in vacuo, and the residue was purified by flash column chromatography on silica gel eluting with a 50-100% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give methyl 4-chloro-3-{[(4,6-diethyl-2-methylpyrimidin-5-yl)carbamothioyl]amino}-2-[(3-hydroxypropyl)amino]benzoate as a yellow solid (3.22 g).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by flash column chromatography on silica gel eluting with a 50-100% ethyl acetate/n-hexane gradient mixture
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6b15f7d925f045e88c4fded4fda46a71
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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