Methylamine → HCID 57985926, compound

HRID 1869193Notes

Reaction equation

HRID 1869193 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH2:8][C:9]([OH:11])=O)[CH:2]=1.C1C[N:24]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)[CH2:23]C1.F[P-](F)(F)(F)(F)F.CN>C(Cl)Cl>[CH3:23][NH:24][C:9](=[O:11])[CH2:8][CH:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:12]1[C:20]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 2724699PyBOPHCID 57985939HCID 57985939, compound

Product 1

HCID 57985926HCID 57985926, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a RT suspension of 3-pyridin-3-yl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propionic acid (810 mg, 3.03 mmol) in DCM (30 mL) was added TEA (0.63 mL, 4.54 mmol) followed by PyBOP (1.73 g, 3.33 mmol) and MeNH2 (2 M in THF, 2.27 mL, 4.54 mmol). After stirring the reaction mixture at RT for 30 min, the beige precipitate was filtered off, and the filtrate was concentrated. The crude residue was purified via flash chromatography (DCM/MeOH/NH4OH) to afford N-Methyl-3-pyridin-3-yl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propionamide as a yellow oil (525 mg).

Workup

  1. filtrationthe beige precipitate was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe crude residue was purified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-3373e9f554864b169cffe444beedbf11
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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