Water → HCID 22672559, compound

HRID 1369568Notes

Reaction equation

HRID 1369568 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:13]=3[C:14](O)=[O:15])=[CH:8][CH:7]=[CH:6][N:5]2[C:22]=1[CH3:23].O.C(Cl)[Cl:26]>C1(C)C=CC=CC=1>[ClH:26].[OH:15][CH2:14][C:13]1[CH:17]=[CH:18][CH:19]=[C:20]([CH3:21])[C:12]=1[CH2:11][NH:10][C:9]1[C:4]2[N:5]([C:22]([CH3:23])=[C:2]([CH3:1])[N:3]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6344DichloromethaneHCID 22672583HCID 22672583, compound

Product 1

HCID 22672559HCID 22672559, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To an icecooled mixture of 2-(((2,3-dimethylimidazo[1,2-a]pyridin-8-yl)amino)methyl)-3-methylbenzoic acid (0.18 g, 0.59,mmol) in toluene (30 ml) was added dropwise Red-A1 (5 ml) in toluene (7 ml) and was stirred at room temperature for 20 h. The mixture was cooled with ice and water (10 ml) and methylene chloride were added. After filtration the filtrate was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using methylene chloride:methanol (100:5) as eluent. The product was solved in methylene chloride/ether and treated with HCl/diethyl ether to give 0.024 g (12%) of the title compound.

Workup

  1. additionwere added
  2. filtrationAfter filtration the filtrate
  3. customwas evaporated under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel
  5. additiontreated with HCl/diethyl ether

Sources & evidence

ORD record
ord-a9595502a1c949ba9cb10ffd068afc56
Source dataset
uspto-grants-2003_06
Patent number
US06579884B1

Reaction notes

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