Triethylamine → 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2',3':4,5]pyrrolo[2,3-b]pyridine-4-carboxamide

HRID 2410689Notes

Reaction equation

HRID 2410689 reaction equation
C([N:3](CC)CC)C.[CH3:8][O:9][C:10]1[N:15]=[C:14]2[NH:16][C:17]3[C:22]([C:23](O)=[O:24])=[CH:21][C:20]([C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)=[N:19][C:18]=3[C:13]2=[CH:12][CH:11]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[Cl-].[NH4+]>CN(C)C=O>[CH3:8][O:9][C:10]1[N:15]=[C:14]2[NH:16][C:17]3[C:22]([C:23]([NH2:3])=[O:24])=[CH:21][C:20]([C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)=[N:19][C:18]=3[C:13]2=[CH:12][CH:11]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 666053457-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2',3':4,5]pyrrolo[2,3-b]pyridine-4-carboxylic acid

Product 1

HCID 666049087-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2',3':4,5]pyrrolo[2,3-b]pyridine-4-carboxamideYield 69.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dimethylformamide (0.6 mL) followed by triethylamine (47 μL, 0.34 mmol) were added to a mixture of 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2′,3′:4,5]pyrrolo[2,3-b]pyridine-4-carboxylic acid (74 mg, 0.21 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodimide hydrochloride (53 mg, 0.28 mmol), 1-hydroxybenzotriazole hydrate (42 mg, 0.28 mmol), and ammonium chloride (18 mg, 0.34 mmol). The reaction mixture was stirred at room temperature for 16 h. The solvent were removed under vacuum and the residue was suspended in about 10 mL of dimethylsulfoxide. The solid was collected by filtration and washed with a little dimethylsulfoxide and water. This was dried under vacuum over solid sodium hydroxide to leave 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2′,3′:4,5]pyrrolo[2,3-b]pyridine-4-carboxamide (51 mg, 66% yield) as a yellow solid. MS (ESI) m/z 349.2 (M+H). 1H NMR (DMSO-d6) δ ppm 11.36 (1H, br. s.), 8.49 (2H, d, J=8.06 Hz), 8.26 (1H, s), 8.20 (2H, d, J=8.56 Hz), 7.86 (1H, br. s.), 7.09 (2H, d, J=8.56 Hz), 6.75 (1H, d, J=8.31 Hz), 4.00 (3H, s), 3.84 (3H, s).

Workup

  1. customThe solvent were removed under vacuum
  2. filtrationThe solid was collected by filtration
  3. washwashed with a little dimethylsulfoxide and water
  4. dry with materialThis was dried under vacuum over solid sodium hydroxide

Sources & evidence

ORD record
ord-c2fc0d88f691439c9482a9f2909da990
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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