Methylamine → HCID 57985914, compound

HRID 1869191Notes

Reaction equation

HRID 1869191 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:9][CH:10]=[C:11]([CH:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][C:14]([OH:16])=O)[C:4]=12.C1C[N:26]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)[CH2:25]C1.F[P-](F)(F)(F)(F)F.CN>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:9][CH:10]=[C:11]([CH:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][C:14]([NH:26][CH3:25])=[O:16])[C:4]=12

Participants

5

Reactant 3

HCID 6329MethylamineHCID 2724699PyBOPHCID 59224308HCID 59224308, compound

Product 1

HCID 57985914HCID 57985914, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a RT suspension of 3-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-3-phenyl-propionic acid (635 mg, 2.14 mmol) in DCM (20 mL) was added TEA (0.45 mL, 3.21 mmol). To this mixture was added PyBOP (1.22 g, 2.35 mmol) and MeNH2 (2 M in THF, 1.60 mL, 3.21 mmol). The resulting mixture was stirred at RT for 30 min, and the white precipitate was collected by filtration to afford 3-(4-Methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-methyl-3-phenyl-propionamide in 72% yield (477 mg).

Workup

  1. filtrationthe white precipitate was collected by filtration

Sources & evidence

ORD record
ord-9377c9d9a8324cc685ab0ea0d98c03e4
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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