Triethylamine → N-[1-(3-bromophenyl)-2-(4-morpholinyl)ethyl]-2-(6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-N-methylacetamide

HRID 2114348노트

반응식

HRID 2114348 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:16][CH3:17])[CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=1.[Cl:18][C:19]1[C:20]([Cl:33])=[CH:21][C:22]2[O:27][CH2:26][CH2:25][N:24]([CH2:28][C:29]([OH:31])=O)[C:23]=2[CH:32]=1.CN([P+]([O:44]N1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>ClCCl.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([N:16]([CH3:17])[C:29](=[O:31])[CH2:28][N:24]2[C:23]3[CH:32]=[C:19]([Cl:18])[C:20]([Cl:33])=[CH:21][C:22]=3[O:27][CH2:26][C:25]2=[O:44])[CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 57418663HCID 57418663, 화합물HCID 57501274[1-(3-Bromophenyl)-2-(4-morpholinyl)ethyl]methylamine

생성물 1

HCID 57457162N-[1-(3-bromophenyl)-2-(4-morpholinyl)ethyl]-2-(6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-N-methylacetamide수율 56%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

A mixture of [1-(3-bromophenyl)-2-(4-morpholinyl)ethyl]methylamine (3.06 g, 10.2 mmol) and (6,7-dichloro-2,3-dihydro-4H-1,4-benzoxazin-4-yl)acetic acid (2.82 g, 10.2 mmol) was dissolved in a mixture of dichloromethane and DMF (1:1, 100 mL). BOP Reagent (7.16 g, 16.6 mmol) was added followed by triethylamine (4.36 g, 43.2 mmol). The resultant mixture was stirred at room temperature for 16 h. The mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (150 mL) and extracted with 5% NaHCO3 (150 mL) and brine (150 mL). The organic layer was dried over MgSO4, and concentrated. The residue was recrystallized in ether, and the crystal was collected by filtration to give the title compound as a white solid (3.17 g, 56%). MS (ESI): 556.2 [M+H]+.

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
  3. extractionextracted with 5% NaHCO3 (150 mL) and brine (150 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was recrystallized in ether
  7. filtrationthe crystal was collected by filtration

출처 및 근거

ORD 기록
ord-921a331143384d36b545b9ed0d5f0f2e
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432258B2

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