Acetic Acid → HCID 44188037, compound

HRID 2063929Notes

Reaction equation

HRID 2063929 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.[F:17][C:18]1[CH:19]=[C:20]([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:21]=[C:22]([F:24])[CH:23]=1.C(O)(=O)C.ClC(Cl)C.C([BH3-])#N>>[F:17][C:18]1[CH:19]=[C:20]([CH:25]2[CH2:26][CH2:27][N:28]([CH2:1][C:3]3[CH:4]=[C:5]([C:14]([OH:16])=[O:15])[C:6](=[O:13])[N:7]4[C:12]=3[CH:11]=[CH:10][CH:9]=[CH:8]4)[CH2:29][CH2:30]2)[CH:21]=[C:22]([F:24])[CH:23]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 498716Cyano-borohydrideHCID 166793124-(3,5-Difluorophenyl)piperidineHCID 772314531-formyl-4-oxo-4H-quinolizine-3-carboxylic acid

Product 1

HCID 44188037HCID 44188037, 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 (35 mg, 0.16 mmol), 4-(3,5-difluorophenyl)piperidine (45.4 mg, 0.23 mmol), glacial acetic acid (0.055 mL, 0.97 mmol) and 0.80 mL of dichloroethane was stirred vigorously. To the stirring mixture was added resin-bound MP-cyanoborohydride (20.3 mg, 0.32 mmol). The mixture was heated via Emrys Optimizer™ microwave to 120° C. for 30 minutes. The reaction was filtered, providing material, which was purified by reverse phase HPLC to yield the title compound that gave a high resolution mass spectrum (ES+) m/z of 399.1512 calculated for M+H+ [C22H20F2N2O3: 399.1515].

Workup

  1. filtrationThe reaction was filtered
  2. customproviding material, which
  3. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-10d536a30c79443e925269f3bdda03b4
Source dataset
uspto-grants-2012_10
Patent number
US08288409B2

Reaction notes

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