Sodium Bicarbonate → HCID 67410537, compound

HRID 2112161Notes

Reaction equation

HRID 2112161 reaction equation
Cl.[F:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[N:16]=[CH:15]3)=[C:7]([CH:10]=1)[CH2:8][NH2:9].[C:22]([O-:25])(O)=O.[Na+]>CCOC(C)=O>[F:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[N:16]=[CH:15]3)=[C:7]([CH:10]=1)[CH2:8][NH:9][CH2:8][C:7]1[CH:10]=[CH:3][C:4]([O:25][CH3:22])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 57484115HCID 57484115, compound

Product 1

HCID 67410537HCID 67410537, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Intermediate (5t) (136 mg, 0.442 mmol; prepared as in Example 106, Step A) was dissolved in EtOAc (100 mL) and neutralized with saturated NaHCO3 then washed with brine, dried over MgSO4 and evaporated under reduced pressure to obtain the free amine. The free amine was dissolved in 1,2-dichloroethane (5 mL) and p-anisaldehyde was added to the solution at room temperature. After 2 hours of stirring, the solution was evaporated under reduced pressure. The residue was dissolved in MeOH (5 mL) and cooled to 0° C. Sodium borohydride was added to the solution at 0° C. After 40 minutes of stirring at 0° C., the reaction mixture was quenched with several drops of acetic acid at 0° C., then the reaction mixture was evaporated under reduced pressure. The residue was diluted with EtOAc (50 mL) and neutralized with saturated NaHCO3 and washed with brine, dried over MgSO4 and evaporated to obtain a crude oil, which was purified on silica gel with EtOAc/hexane (1:1) with 1% Et3N to afford compound (29t) as a color less oil (139 mg, 80% yield). 1HNMR (400 MHz, CDCl3) δ 7.85 (s, 1H), 7.34 (d, J=9.4 Hz, 1H), 7.28 (d, J=7.0 Hz, 1H), 7.23-7.15 (m, 2H), 7.13-7.06 (m, 2H), 6.92-6.85 (m, 2H), 6.84-6.78 (m, 2H), 4.61 (s, 1H), 4.06 (s, 3H), 3.82 (s, 2H), 3.77 (s, 3H), 3.72 (s, 2H) ppm.

Workup

  1. washthen washed with brine
  2. dry with materialdried over MgSO4
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-211f597808104990898eae4202531ead
Source dataset
uspto-grants-2009_04
Patent number
US07521447B2

Reaction notes

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