Triethylamine → HCID 49764439, compound

HRID 1677396Notes

Reaction equation

HRID 1677396 reaction equation
[CH3:1][C:2]1([C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=4)[N:17]=3)[NH:12][CH:11]=2)=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.N1(O)C2C=CC=CC=2N=N1.[C:41]([CH2:43][C:44](O)=[O:45])#[N:42].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>ClCCl>[CH3:1][C:2]1([C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=4)[N:17]=3)[NH:12][CH:11]=2)=[O:9])[CH2:7][CH2:6][CH2:5][N:4]([C:44](=[O:45])[CH2:43][C:41]#[N:42])[CH2:3]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 9740Cyanoacetic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 44206942HCID 44206942, compound

Product 1

HCID 49764439HCID 49764439, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (3-methyl-piperidin-3-yl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone (11 mg, 0.27 mmol), benzotriazol-1-ol (4.0 mg, 0.03 mmol), 2-cyanoacetic acid (3 mg, 0.04 mmol), and (3-dimethylamino-propyl)-ethyl-carbodiimide hydrogen chloride (6.0 mg, 0.03 mmol) in anhydrous dichloromethane was treated with triethylamine (0.01 ml, 0.08 mmol) and allowed to stir at room temperature overnight. The reaction mixture was partitioned between dichloromethane/water and the organic layers were collected, dried over MgSO4, filtered, and concentrated. The residue was purified by preparative thin layer chromatography using 0.25:4.75:95 concentrated aqueous NH4OH: MeOH: dichloromethane as eluant to provide 5 mg (42%) of 3-{3-methyl-3-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-piperidin-1-yl}-3-oxo-propionitrile as a light yellow solid. M+H 578.

Workup

  1. customThe reaction mixture was partitioned between dichloromethane/water
  2. customthe organic layers were collected
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-902920ba83dc4fa3ac658236743242d0
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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