Sodium Acetate → HCID 21899130, compound

HRID 1868618Notes

Reaction equation

HRID 1868618 reaction equation
[CH:1]([C:3]1[CH:30]=[CH:29][C:6]2[N:7]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:8]([NH:10][C:11](=[O:22])[C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=3)=[N:9][C:5]=2[CH:4]=1)=O.CC([O-])=O.[Na+].Cl.[NH2:37][CH2:38][CH2:39][CH2:40][C:41]([O:43]CC)=O.[BH3-]C#N.[Na+]>CC(O)=O.C([O-])(O)=O.[Na+].CCOC(C)=O.CO>[O:43]=[C:41]1[CH2:40][CH2:39][CH2:38][N:37]1[CH2:1][C:3]1[CH:30]=[CH:29][C:6]2[N:7]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:8]([NH:10][C:11](=[O:22])[C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:20])[F:21])[CH:13]=3)=[N:9][C:5]=2[CH:4]=1

Participants

9

Reactant 4

HCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 126496614-Aminobutyrate ethyl hydrochlorideHCID 21899143HCID 21899143, compound

Product 1

HCID 21899130HCID 21899130, compoundYield 57%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

and (e) To a suspension of 409 mg N-(5-Formyl-1-phenyl-1H-benzoimidazol-2-yl)-3-trifluoromethylbenzamide (1.00 mmol, 1.00 equiv) prepared above in Example 7 in 40 mL of 1:9 HOAc:MeOH, 0.205 g NaOAc (2.50 mmol, 2.50 equiv), and 0.84 g ethyl 4-aminobutyrate hydrochloride (5.00 mmol, 5.00 equiv) was added 0.138 g NaCNBH3 (2.00 mmol, 2.00 equiv). The pink suspension was allowed to stir 20 h, after which time the resulting brown solution was diluted with 50 mL sat. NaHCO3 and 50 mL EtOAc. The aqueous layer was extracted (2×EtOAc) and the combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. Purification by flash chromatography (SiO2, 1-2% MeOH/CH2Cl2 with 1% aq. NH4OH) gave 300 mg of the product as a colorless solid (0.57 mmol). A solution of 105 mg of this product (0.20 mmol, 1.00 equiv) in 20 mL toluene and 2 mL HOAc was heated to reflux temperature for 1 h. The solution was concentrated under reduced pressure and purified by flash chromatography (SiO2, 2-5% MeOH/CH2Cl2 with 1% aq. NH4OH) to give 80 mg of the product as a colorless solid (0.17 mmol). 1H NMR (CDCl3, 400 MHz) δ 13.03 (s, 1H), 8.31 (s, 1H), 8.28 (d, J=7.8 Hz, 1H), 7.85 (d, J=7.7 Hz, 1H), 7.65-7.75 (m, 5H), 8.26 (t, J=7.1 Hz, 1H), 7.53 (s, 1H), 7.16 (m, 2H), 4.47 (s, 2H), 3.26 (t, J=7.0 Hz, 2H), 2.31 (t, J=8.0 Hz, 2H), 1.94 (m, 2H).

Workup

  1. extractionThe aqueous layer was extracted (2×EtOAc)
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash chromatography (SiO2, 1-2% MeOH/CH2Cl2 with 1% aq. NH4OH)

Sources & evidence

ORD record
ord-cf04aa5800b344849b22458df744c0f1
Source dataset
uspto-grants-2009_12
Patent number
US07635774B2

Reaction notes

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