Acetic Acid → HCID 44232443, 화합물

HRID 1921232노트

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HRID 1921232 반응식
[CH:1]([C:3]1[CH:4]=[C:5]([C:14]([OH:16])=[O:15])[C:6](=[O:13])[N:7]2[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]2)=O.[Cl:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH2:24][NH:23][CH2:22][CH2:21]2.C(O)(=O)C.ClC(Cl)C.C([BH3-])#N>>[Cl:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH2:24][N:23]([CH2:1][C:3]1[CH:4]=[C:5]([C:14]([OH:16])=[O:15])[C:6](=[O:13])[N:7]3[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]3)[CH2:22][CH2:21]2

참가 물질

6

반응물 5

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 498716Cyano-borohydrideHCID 117895946-Chloro-1,2,3,4-tetrahydroisoquinolineHCID 772314531-formyl-4-oxo-4H-quinolizine-3-carboxylic acid

생성물 1

HCID 44232443HCID 44232443, 화합물

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온도
120 °C

실험 절차

In a 2-5 mL Emrys™ process vial, a mixture of the 1-formyl-4-oxo-4H-quinolizine-3-carboxylic acid (76 mg, 0.35 mmol), 6-chloro-1,2,3,4-tetrahydroisoquinoline (82 mg, 0.49 mmol), glacial acetic acid (0.12 mL, 2.1 mmol) and 1.8 mL of dichloroethane was stirred vigorously. To the stirring mixture was added resin-bound MP-cyanoborohydride (343 mg, 0.70 mmol). The mixture was heated via Emrys Optimizer™ microwave to 120° C. for 30 minutes. Filtration and solvent removal provided material, which was subjected to preparative reverse phase HPLC. Collection of product containing fractions and removal of solvent yielded the title compound that gave a proton NMR spectrum consistent with theory and a high resolution mass spectrum (ES+) m/z of 369.1011 calculated for M+H+ [C20H17Cl1N2O3: 369.1001]: 1H NMR (500 MHz, CD3OD) δ 9.59 (d, J=7.1 Hz, 1H), 8.74 (s, 1H), 8.40 (d, J=8.8 Hz, 1H), 8.18 (t, J=73 Hz, 1H), 7.73 (t, J=6.6 Hz, 1H), 7.32 (s, 1H), 7.27 (d, J=8.3 Hz, 1H), 7.14 (d, J=8.6 Hz, 1H), 4.87 (s, 2H), 4.47 (s, 2H), 3.69 (bs, 2H), 3.20 (t, J=6.0 Hz, 2H).

후처리

  1. filtrationFiltration and solvent removal
  2. customprovided material, which
  3. customCollection of product
  4. additioncontaining
  5. customfractions and removal of solvent

출처 및 근거

ORD 기록
ord-c7b8c59fb17d4ea9982150af3e656cd9
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173672B2

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