Water → HCID 45279720, compound

HRID 2060741Notes

Reaction equation

HRID 2060741 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[C:9]2[CH:10]=[C:11]([C:20]([OH:22])=[O:21])[C:12](=[O:19])[N:13]3[C:18]=2[CH:17]=[CH:16][CH:15]=[CH:14]3)=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:10]=[C:11]([C:20]([OH:22])=[O:21])[C:12](=[O:19])[N:13]3[C:18]=2[CH:17]=[CH:16][CH:15]=[CH:14]3)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 45279723HCID 45279723, compound

Product 1

HCID 45279720HCID 45279720, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[(4-chlorophenyl)(hydroxy)methyl]-4-oxo-4H-quinolizine-3-carboxylic acid (0.300 mg, 0.910 mmol) in 5 mL of CH2Cl2 was added triethylsilane (0.29 mL, 1.8 mmol) and trifluoroacetic acid (0.35 mL, 4.5 mmol). After 1.5 h, 10 mL of water was added, and the reaction was extracted with CH2Cl2, dried over sodium sulfate, filtered, and concentrated in vacuo. The resultant residue was subjected to purification via reverse phase HPLC to yield the title compound that gave a mass ion (ES+) of 313.96 for M+H+. 1H NMR (400 MHz, CD3OD) δ 9.49 (d, J=7.1 Hz, 1H), 8.40 (s, 1H), 8.07 (d, J=9.1 Hz, 1H), 7.99-7.94 (m, 1H), 7.62-7.58 (m, 1H), 7.32 (d, J=8.5 Hz, 2H), 7.22 (d, J=8.8 Hz, 1H), 4.32 (s, 2H).

Workup

  1. extractionthe reaction was extracted with CH2Cl2
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was subjected to purification via reverse phase HPLC

Sources & evidence

ORD record
ord-ea0081a5530b4cacbec4151ea553c827
Source dataset
uspto-grants-2012_10
Patent number
US08278453B2

Reaction notes

Loading…