Benzylethanolamine → HCID 59285904, compound

HRID 1011586Notes

Reaction equation

HRID 1011586 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].[NH2:16][C:17]([NH:19][C:20]1[NH:21][C:22]([C:28]2[CH:33]=[CH:32][C:31]([CH:34]=O)=[CH:30][CH:29]=2)=[CH:23][C:24]=1[C:25]([NH2:27])=[O:26])=[O:18].C(=O)([O-])O.[Na+]>CN(C)C=O.O.C(O)(=O)C>[NH2:16][C:17]([NH:19][C:20]1[NH:21][C:22]([C:28]2[CH:29]=[CH:30][C:31]([CH2:34][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][CH2:10][OH:11])=[CH:32][CH:33]=2)=[CH:23][C:24]=1[C:25]([NH2:27])=[O:26])=[O:18]

Participants

8

Reactant 4

HCID 4348BenzylethanolamineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 59285919HCID 59285919, compound

Product 1

HCID 59285904HCID 59285904, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Acetic acid (30 μl N-benzylethanolamine (79 μL, 0.55 mmol) and sodium cyanoborohydride (35 mg, 0.55 mmol) were added to a solution of 2-aminocarbonylamino-5-(4-formylphenyl)pyrrole-3-carboxamide (Compound No. 14-1, 50 mg, 0.18 mmol) in N,N-dimethylformamide (3 mL) and the mixture was stirred overnight at room temperature. Saturated aqueous sodium hydrogencarbonate (10 mL) and water (10 mL) were added to the reaction solution, extracted with ethyl acetate (20 mL). The organic layer was washed with brine (10 mL), dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, the obtained residue was purified by silica gel column chromatography to give the target compound (26 mg) as a colorless solid (Yield 36%)

Workup

  1. extractionextracted with ethyl acetate (20 mL)
  2. washThe organic layer was washed with brine (10 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d31e3a0728874e2683177b51304525da
Source dataset
uspto-grants-2011_07
Patent number
US07977371B2

Reaction notes

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