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

HRID 1876289
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HRID 1876289 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매

1
HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-734a6b6071454d9790d848dd4887acc3
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08309597B2

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