Ammonia → 2-(3-chlorophenyl)-7-(4-morpholinyl)-5H-pyrido[2',3':4,5]pyrrolo[2,3-b]pyridine-4-carboxamide

HRID 2410755Notes

Reaction equation

HRID 2410755 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([C:27]([O:29]C)=O)[C:11]3[NH:25][C:14]4=[N:15][C:16]([N:19]5[CH2:24][CH2:23][O:22][CH2:21][CH2:20]5)=[CH:17][CH:18]=[C:13]4[C:12]=3[N:26]=2)[CH:5]=[CH:6][CH:7]=1.[NH3:31]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([C:27]([NH2:31])=[O:29])[C:11]3[NH:25][C:14]4=[N:15][C:16]([N:19]5[CH2:24][CH2:23][O:22][CH2:21][CH2:20]5)=[CH:17][CH:18]=[C:13]4[C:12]=3[N:26]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66605303methyl 2-(3-chlorophenyl)-7-(4-morpholinyl)-5H-pyrido[2',3':4,5]pyrrolo[2,3-b]pyridine-4-carboxylate

Product 1

HCID 666049412-(3-chlorophenyl)-7-(4-morpholinyl)-5H-pyrido[2',3':4,5]pyrrolo[2,3-b]pyridine-4-carboxamideYield 19%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 2-(3-chlorophenyl)-7-(4-morpholinyl)-5H-pyrido[2′,3′:4,5]pyrrolo[2,3-b]pyridine-4-carboxylate (50 mg, 0.12 mmol) in a solution of 7 N NH3 in MeOH (5 mL) in a sealed microwave vial was heated at 80° C. for 48 hr. Filtration gave 2-(3-chlorophenyl)-7-(4-morpholinyl)-5H-pyrido[2′,3′:4,5]pyrrolo[2,3-b]pyridine-4-carboxamide (10 mg, 0.022 mmol, 19% yield) as a yellow solid. MS (ESI) m/z 408 (M+H). 1H NMR (DMSO-d6) δ ppm 10.97 (s, 1H), 8.53 (br. s., 1H), 8.19-8.44 (m, 4H), 7.88 (br. s., 1H), 7.41-7.63 (m, 2H), 6.87 (br. s., 1H), 3.56-3.88 (m, 8H).

Workup

  1. filtrationFiltration

Sources & evidence

ORD record
ord-e20a7cf2c06b40819733fd7c01c1d545
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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