Methylamine → HCID 57985894, compound

HRID 1869202Notes

Reaction equation

HRID 1869202 reaction equation
[C:1]1([CH:7]([C:12]2[C:16]3[CH:17]=[N:18][CH:19]=[CH:20][C:15]=3[NH:14][CH:13]=2)[CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN.F[P-](F)(F)(F)(F)F.[N:30]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:34]2C=CC=CC=2N=N1>C(Cl)Cl.CN(C=O)C.C([O-])(O)=O.[Na+]>[CH3:34][NH:30][C:9](=[O:11])[CH2:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:12]1[C:16]2[CH:17]=[N:18][CH:19]=[CH:20][C:15]=2[NH:14][CH:13]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 57985915HCID 57985915, compound

Product 1

HCID 57985894HCID 57985894, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 516892Sodium BicarbonateSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a RT suspension of 3-phenyl-3-(1H-pyrrolo[3,2-c]pyridin-3-yl)-propionic acid (1.1 mmol) in DCM/DMF (3/2, 5 mL) was added TEA (0.23 mL, 1.7 mmol) followed by MeNH2 (2 M in THF, 0.83 mL) and benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (0.58 g, 1.3 mmol). The resulting mixture was stirred at RT overnight, diluted with an aqueous solution of NaHCO3, and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (DCM/MeOH/NH40H), affording N-Methyl-3-phenyl-3-(1H-pyrrolo[3,2-c]pyridin-3-yl)-propionamide (0.16 g).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified via flash chromatography (DCM/MeOH/NH40H)

Sources & evidence

ORD record
ord-cd5692ba9e0e4c3c97db91f3938136eb
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

Loading…