Methylamine → 3-Chloro-N-isopropyl-5-methoxy-N-(2-methylcarbamoyl-ethyl)-benzamide

HRID 2268599Notes

Reaction equation

HRID 2268599 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1)[C:5]([N:7]([CH:13]([CH3:15])[CH3:14])[CH2:8][CH2:9][C:10](O)=[O:11])=[O:6].[CH3:21][N:22](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.CN>CN(C=O)C.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1)[C:5]([N:7]([CH:13]([CH3:15])[CH3:14])[CH2:8][CH2:9][C:10](=[O:11])[NH:22][CH3:21])=[O:6]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 183491943-[(3-Chloro-5-methoxy-benzoyl)-isopropyl-amino]-propionic acid

Product 1

HCID 183491573-Chloro-N-isopropyl-5-methoxy-N-(2-methylcarbamoyl-ethyl)-benzamideYield 91.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-[(3-chloro-5-methoxy-benzoyl)-isopropyl-amino]-propionic acid (0.600 g), TBTU (1.28 g) in DMF (10 ml) was added DIPEA (0.696 ml) followed a 2M solution of methylamine in THF (8.0 ml) after 10 min. The reaction mixture was stirred at room temperature for 4 h and then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic phase was washed with further water and 1M aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, water and dried with brine and over sodium sulphate and concentrated under reduced pressure to give the title compound as a brown oil (0.575 g).

Workup

  1. customafter 10 min
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe organic phase was washed with further water and 1M aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, water
  5. dry with materialdried with brine and over sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e05f233ff18c4696b649e5c522de3395
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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