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Dimethylamine → 7-(4-Dimethylcarbamoyl-phenoxy)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester

HRID 1876289
ノート
印刷プレビュー

反応式

HRID 1876289 の反応式
F[B-](F)(F)F.N1(O[C:16](N(C)C)=[N+:17](C)[CH3:18])C2C=CC=CC=2N=N1.[CH2:23]([O:30][C:31]([N:33]1[CH2:42][CH2:41][C:40]2[C:35](=[CH:36][C:37]([O:43][C:44]3[CH:49]=[CH:48][C:47]([C:50]([OH:52])=O)=[CH:46][CH:45]=3)=[CH:38][CH:39]=2)[CH2:34]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CNC.CN1CCOCC1>O1CCCC1>[CH2:23]([O:30][C:31]([N:33]1[CH2:42][CH2:41][C:40]2[C:35](=[CH:36][C:37]([O:43][C:44]3[CH:49]=[CH:48][C:47]([C:50](=[O:52])[N:17]([CH3:18])[CH3:16])=[CH:46][CH:45]=3)=[CH:38][CH:39]=2)[CH2:34]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 674DimethylamineHCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 584938387-(4-Carboxy-phenoxy)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester

生成物 1

HCID 584939027-(4-Dimethylcarbamoyl-phenoxy)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (0.44 g) is added to a solution of 7-(4-carboxy-phenoxy)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester, dimethylamine (2 mol/L in tetrahydrofuran, 0.68 mL), and N-methyl-morpholine (0.41 mL) in tetrahydrofuran (20 mL) chilled in an ice bath. The cooling bath is removed and the resulting mixture is stirred at room temperature for 3 h. Then another portion of dimethylamine (2 mol/L in tetrahydrofuran, 0.70 mL) and 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (0.20 g) are added and the mixture is further stirred for another 4 h. After adding another portion of dimethylamine (2 mol/L in tetrahydrofuran, 0.30 mL), the mixture ist stirred at room temperature overnight. The mixture is concentrated and the residue is purified by chromatography on silica gel (ethyl acetate) to furnish the title compound.

後処理

  1. temperaturechilled in an ice bath
  2. customThe cooling bath is removed
  3. additionThen another portion of dimethylamine (2 mol/L in tetrahydrofuran, 0.70 mL) and 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (0.20 g) are added
  4. stirringthe mixture is further stirred for another 4 h
  5. additionAfter adding another portion of dimethylamine (2 mol/L in tetrahydrofuran, 0.30 mL)
  6. stirringthe mixture ist stirred at room temperature overnight
  7. concentrationThe mixture is concentrated
  8. customthe residue is purified by chromatography on silica gel (ethyl acetate)

出典と根拠

ORDレコード
ord-734a6b6071454d9790d848dd4887acc3
出典データセット
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08309597B2

反応ノート

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