Acetic Acid → HCID 44232443, compound

HRID 1921232Notes

Reaction equation

HRID 1921232 reaction equation
[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

Participants

6

Reactant 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

Product 1

HCID 44232443HCID 44232443, compound

Conditions

Temperature
120 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-c7b8c59fb17d4ea9982150af3e656cd9
Source dataset
uspto-grants-2012_05
Patent number
US08173672B2

Reaction notes

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