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

HRID 2354377ノート

反応式

HRID 2354377 の反応式
[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][C:4]([CH:7]([NH:15][CH3:16])[CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:3][CH:2]=1.[Cl:23][C:24]1[C:25]([Cl:38])=[CH:26][C:27]2[O:32][CH2:31][CH2:30][N:29]([CH2:33][C:34]([OH:36])=O)[C:28]=2[CH:37]=1.CN([P+]([O:49]N1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:2]=[CH:3][C:4]([CH:7]([N:15]([CH3:16])[C:34](=[O:36])[CH2:33][N:29]2[C:28]3[CH:37]=[C:24]([Cl:23])[C:25]([Cl:38])=[CH:26][C:27]=3[O:32][CH2:31][C:30]2=[O:49])[CH2:8][N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)=[CH:5][CH:6]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 57418663HCID 57418663、化合物HCID 57425536[1-(4-Biphenylyl)-2-(4-morpholinyl)ethyl]methylamine

生成物 1

HCID 44561196N-[1-(4-biphenylyl)-2-(4-morpholinyl)ethyl]-2-(6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-N-methylacetamide収率 59.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of [1-(4-biphenylyl)-2-(4-morpholinyl)ethyl]methylamine (3.67 g, 12.4 mmol) and (6,7-dichloro-2,3-dihydro-4H-1,4-benzoxazin-4-yl)acetic acid (3.42 g, 12.4 mmol) in DMF (50 mL) was added BOP Reagent (8.23 g, 18.6 mmol) followed by triethylamine (3.76 g, 37.2 mmol). The resultant mixture was stirred at room temperature for 16 h. The mixture was concentrated under reduced pressure, diluted with ethyl acetate (150 mL), and extracted with 5% NaHCO3 (100 mL) and brine (100 mL). The organic layer was dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography (330 g redisep column, silica 40 um, 60 A, 100 ml/min, A: MeOH, B: CH2Cl2, A: 1% for 30 min) to give 4.08 g (59%) of title compound as a white solid. MS (ES) m/e 554.4 [M+H]+.

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with ethyl acetate (150 mL)
  3. extractionextracted with 5% NaHCO3 (100 mL) and brine (100 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (330 g redisep column, silica 40 um, 60 A, 100 ml/min

出典と根拠

ORDレコード
ord-760edc8c264f42c1a83954c04dc0cb6c
出典データセット
uspto-grants-2010_07
特許番号
US07749998B2

反応ノート

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