Sodium Bicarbonate → HCID 45109842, compound

HRID 1256273Notes

Reaction equation

HRID 1256273 reaction equation
[C:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][C:10](=[O:14])[NH:11]2)=[CH:6][CH:5]=1)(=O)[CH3:2].[Cl:15][C:16]1[CH:17]=[C:18]([CH:28]=[CH:29][C:30]=1[F:31])[C:19]([NH:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:20].[BH3-]C#N.[Na+].C([O-])(O)=O.[Na+]>CC(O)=O.CO>[Cl:15][C:16]1[CH:17]=[C:18]([CH:28]=[CH:29][C:30]=1[F:31])[C:19]([NH:21][CH:22]1[CH2:23][CH2:24][N:25]([CH:1]([C:4]2[CH:13]=[C:12]3[C:7]([CH2:8][CH2:9][C:10](=[O:14])[NH:11]3)=[CH:6][CH:5]=2)[CH3:2])[CH2:26][CH2:27]1)=[O:20]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydride2×HCID 13120789HCID 13120789, compoundHCID 67130841HCID 67130841, compound

Product 1

HCID 45109842HCID 45109842, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a MeOH solution (15 mL) of the compound (206 mg) obtained in Step 51-2, the compound (560 mg) obtained in Step 51-3 and AcOH (327 mg), NaBH3CN (274 mg) was added at room temperature and the mixture was refluxed for 12 hours. After the reaction mixture was cooled to room temperature, NaBH3CN (274 mg) was added and the mixture was refluxed for 72 hours. After a saturated aqueous NaHCO3 solution was added, a water layer and an organic layer were separated. The water layer was extracted three times with CHCl3. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography [(silica gel 60 N, mobile phase: MeOH/CHCl3=0/100 to 20/80; v/v) and (Chromatorex NH, mobile phase MeOH/CHCl3=0/100 to 10/90; v/v) in this order] to obtain the titled compound (7 mg, a colorless solid).

Workup

  1. temperaturethe mixture was refluxed for 12 hours
  2. temperaturethe mixture was refluxed for 72 hours
  3. customa water layer and an organic layer were separated
  4. extractionThe water layer was extracted three times with CHCl3
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography [(silica gel 60 N, mobile phase: MeOH/CHCl3=0/100 to 20/80; v/v) and (Chromatorex NH, mobile phase MeOH/CHCl3=0/100 to 10/90; v/v) in this order]

Sources & evidence

ORD record
ord-396211afa7634ae6a90419e46f92bab3
Source dataset
uspto-grants-2013_06
Patent number
US08461182B2

Reaction notes

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