Dimethylamine → HCID 53262153, compound

HRID 79444

Reaction equation

HRID 79444 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([CH2:8][N:9]2[C:17]3[C:12](=[C:13]([NH:18][C:19]([C:21]4[N:25]5[CH:26]=[CH:27][C:28]([C:30]6[O:31][C:32]([CH:35]=O)=[CH:33][CH:34]=6)=[CH:29][C:24]5=[N:23][CH:22]=4)=[O:20])[CH:14]=[CH:15][CH:16]=3)[C:11]([CH2:37][CH3:38])=[N:10]2)=[N:3]1.C1COCC1.[CH3:44][NH:45][CH3:46].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CO>[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([CH2:8][N:9]2[C:17]3[C:12](=[C:13]([NH:18][C:19]([C:21]4[N:25]5[CH:26]=[CH:27][C:28]([C:30]6[O:31][C:32]([CH2:35][N:45]([CH3:46])[CH3:44])=[CH:33][CH:34]=6)=[CH:29][C:24]5=[N:23][CH:22]=4)=[O:20])[CH:14]=[CH:15][CH:16]=3)[C:11]([CH2:37][CH3:38])=[N:10]2)=[N:3]1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 86672218N-(1-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)-7-(5-formylfuran-2-yl)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 53262153HCID 53262153, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N-(1-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)-7-(5-formylfuran-2-yl)imidazo[1,2-a]pyridine-3-carboxamide (36 mg) in 1 mL of a 1:1 DCM:THF mixture was treated at ambient temperature with excess 2.0 M dimethylamine solution in MeOH. The reaction mixture was stirred at ambient temperature for 30 minutes. A large excess of sodium triacetoxyborohydride (10 equivalents) was added, and the reaction stirred at ambient temperature for 4 hours. The reaction mixture was concentrated under reduced pressure, dissolved in a small amount of MeOH, and subjected to preparative thin-layer chromatography with a 2% 7N ammonia-MeOH, 8% MeOH in DCM solution as eluent to give the desired product (12.8 mg). MS (ES+APCI) m/z=537 (M+H) detected.

Workup

  1. stirringthe reaction stirred at ambient temperature for 4 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutiondissolved in a small amount of MeOH

Sources & evidence

ORD record
ord-c78e1993506b4f43a8b2b7551bf12a33
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Linked notes

Loading…