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 2114348ノート

反応式

HRID 2114348 の反応式
[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

参加物

7

反応物 4

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

生成物 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-methylacetamide収率 56%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-921a331143384d36b545b9ed0d5f0f2e
出典データセット
uspto-grants-2008_10
特許番号
US07432258B2

反応ノート

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