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

HRID 2268599노트

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HRID 2268599 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e05f233ff18c4696b649e5c522de3395
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06326386B1

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