Methyl 5-Amino-2-chlorobenzoate → HCID 67116665, compound

HRID 1846074Notes

Reaction equation

HRID 1846074 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][C:13]([C:15]2([CH3:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:14])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:22][C:23]1[CH:24]=[CH:25][C:26]([Cl:33])=[C:27]([CH:32]=1)[C:28]([O:30][CH3:31])=[O:29]>C1COCC1>[Cl:33][C:26]1[CH:25]=[CH:24][C:23]([NH:22][C:4](=[O:5])[C:3]2[CH:7]=[C:8]([CH2:11][NH:12][C:13]([C:15]3([CH3:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[O:14])[CH:9]=[CH:10][C:2]=2[CH3:1])=[CH:32][C:27]=1[C:28]([O:30][CH3:31])=[O:29]

Participants

4

Reactant 2

HCID 5200412Methyl 5-Amino-2-chlorobenzoateHCID 86658665HCID 86658665, compound

Product 1

HCID 67116665HCID 67116665, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 2-methyl-5-[(1-methylcyclohexylcarbonylamino)methyl]benzoyl chloride (0.266 g, 0.864 mmol) in 5 mL THF was added to methyl 5-amino-2-chloro-benzoate (0.160 g, 0.864 mmol) and 0.42 mL TEA in 10 mL THF. The mixture was stirred overnight and concentrated. EtOAc was added to the residue and the organic phase was washed with water and 2 M aq. HCl solution and dried with Na2SO4. The crude mixture was purified via MPLC. Yield: 0.21 g (53%). MS [M+H]+=457 (Cl isotope pattern); TLC: Rf=0.44 (silica gel, DCM:EtOH 19:1).

Workup

  1. concentrationconcentrated
  2. additionEtOAc was added to the residue
  3. washthe organic phase was washed with water and 2 M aq. HCl solution
  4. dry with materialdried with Na2SO4
  5. customThe crude mixture was purified via MPLC

Sources & evidence

ORD record
ord-c270e29c0ac34bdcb30b7fdf19d2fbbd
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

Loading…