Methylamine → HCID 57985918, compound

HRID 1869198Notes

Reaction equation

HRID 1869198 reaction equation
[C:1]1([CH:7]([C:12]2[C:16]3=[N:17][CH: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([O-])(O)=O.[Na+]>CN(C=O)C>[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=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[NH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 57985937HCID 57985937, compound

Product 1

HCID 57985918HCID 57985918, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a RT solution of 3-phenyl-3-(1H-pyrrolo[3,2-b]pyridin-3-yl)-propionic acid (150 mg, 0.56 mmol) in DMF (2 mL) was added MeNH2 (2 M in THF, 0.85 mL, 1.7 mmol) followed by benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (300 mg, 0.67 mmol) and TEA (0.12 mL, 0.85 mmol). The mixture was stirred at RT for 3 h, then a saturated solution of NaHCO3 was added, and the mixture was extracted 3 times with EtOAc. The combined organic layers were dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (DCM/MeOH/NH4OH), affording N-Methyl-3-phenyl-3-(1H-pyrrolo[3,2-b]pyridin-3-yl)-propionamide.

Workup

  1. extractionthe mixture was extracted 3 times with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-094c37dc8ccb46839795c50743e65cb4
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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