Acetic Acid → HCID 89662801, compound

HRID 1479083Notes

Reaction equation

HRID 1479083 reaction equation
Cl.[Cl:2][C:3]1[C:11]([CH3:12])=[N:10][C:9]2[N:5]([N:6]=[C:7]3[CH2:15][N:14]([C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[O:24][CH:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH:26]4[F:31])=[O:17])[CH2:13][C:8]3=2)[C:4]=1[CH3:32].C=O.[C:35](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CC(O)=O>ClCCCl.C([O-])([O-])=O.[Na+].[Na+]>[Cl:2][C:3]1[C:11]([CH3:12])=[N:10][C:9]2[N:5]([N:6]=[C:7]3[CH2:15][N:14]([C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[O:24][CH:25]4[CH2:30][CH2:29][N:28]([CH3:35])[CH2:27][CH:26]4[F:31])=[O:17])[CH2:13][C:8]3=2)[C:4]=1[CH3:32]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 131736552HCID 131736552, compound

Product 1

HCID 89662801HCID 89662801, compoundYield 16.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of (6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]inden-2-yl)-[2-(3-fluoro-piperidin-4-yloxy)-phenyl]-methanone hydrochloride (124 mg; 0.26 mmol; 1 eq.), paraformaldehyde (70 mg; 0.78 mmol; 1 eq.), sodium triacetoxyborohydride (110 mg; 0.52 mmol; 2 eq.) and AcOH (30 μL; 0.52 mmol; 2 eq.) in DCE (1.5 mL) was stirred at reflux for 1.5 hour. The reaction mixture was diluted with sat. aq. Na2CO3 and extracted with EA (3×). The combined organic layer was dried over magnesium sulfate and concentrated in vacuo. Purification by mass directed preparative HPLC afforded the title compound (20 mg, 6%) as a white solid. HPLC (max plot) 97.0%, Rt 2.70 min. UPLC/MS: (MS+) 458.4 ([M+H]+).

Workup

  1. temperatureat reflux for 1.5 hour
  2. extractionextracted with EA (3×)
  3. dry with materialThe combined organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by mass

Sources & evidence

ORD record
ord-bb3f18bca8ef44e797cfbbabf8dec335
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

Loading…