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

HRID 2354332ノート

反応式

HRID 2354332 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:15][CH3:16])[CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[Cl:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[Cl:28])[N:24]([CH2:29][C:30]([OH:32])=O)[C:23](=[O:33])[CH2:22]C2.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>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:15]([CH3:16])[C:30](=[O:32])[CH2:29][N:24]2[C:25]3[CH:26]=[C:27]([Cl:28])[C:18]([Cl:17])=[CH:19][C:20]=3[O:44][CH2:22][C:23]2=[O:33])[CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 57418662(6,7-dichloro-2-oxo-3,4-dihydro-1(2H)-quinolinyl)acetic acidHCID 57425537[1-(4-Bromophenyl)-2-(1-pyrrolidinyl)ethyl]methylamine

生成物 1

HCID 57488849N-[1-(4-bromophenyl)-2-(1-pyrrolidinyl)ethyl]-2-(6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-N-methylacetamide収率 25%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of [1-(4-bromophenyl)-2-(1-pyrrolidinyl)ethyl]methylamine (1.61 g, 5.68 mmol) and (6,7-dichloro-2-oxo-3,4-dihydro-1(2H)-quinolinyl)acetic acid (1.73 g, 6.25 mmol) in DMF (20 mL) was added BOP Reagent (3.77 g, 8.52 mmol) and triethylamine (1.72 g, 17.3 mmol). The resultant mixture was stirred at room temperature for 16 h. The mixture was concentrated under reduce pressure. The residue was diluted with ethyl acetate (100 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 (120 g redisep column, silica 40 um, 60 A, 85 ml/min, A: MeOH, B: CH2Cl2, A: 1% for 20 min) to give 0.76 g (25%) title compound as yellow solid. MS (ES) m/e 545.4 [M+H]+.

後処理

  1. concentrationThe mixture was concentrated
  2. additionThe residue was diluted with ethyl acetate (100 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 (120 g redisep column, silica 40 um, 60 A, 85 ml/min

出典と根拠

ORDレコード
ord-2d38b5ae9433436faaf6a2b41ec00005
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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