Water → 2,3-Dimethyl-8-(2,6-dimethylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamide

HRID 427491

Reaction equation

HRID 427491 reaction equation
S(O)(=O)(=O)C.[NH2:6][C:7]1[C:8]2[N:9]([C:16]([CH3:20])=[C:17]([CH3:19])[N:18]=2)[CH:10]=[C:11]([C:13]([NH2:15])=[O:14])[CH:12]=1.[CH2:21]([C:23]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31]C)[C:24]=1[CH2:25]Cl)C.C(N(C(C)C)CC)(C)C.O>CN(C)C=O.C(Cl)Cl>[CH3:19][C:17]1[N:18]=[C:8]2[C:7]([NH:6][CH2:25][C:24]3[C:27]([CH3:31])=[CH:28][CH:29]=[CH:30][C:23]=3[CH3:21])=[CH:12][C:11]([C:13]([NH2:15])=[O:14])=[CH:10][N:9]2[C:16]=1[CH3:20]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 183574358-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide mesylateHCID 183574492-(Chloromethyl)-1,3-diethylbenzene

Product 1

HCID 97972452,3-Dimethyl-8-(2,6-dimethylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamideYield 53.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

8-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide mesylate (4.0 g, 10.7 mmol), 2,6-diethylbenzylchloride (1.8 g, 9.9 mmol), diisopropylethylamin (3.0 g, 23.3 mmol) were stirred in dimethylformamide (20 ml) at 50° C. overnight and at 70° C. for 3 h. Water (60 ml) and methylene chloride were added and the organic layer was separated, dried and evaporated under reduced pressure. The residue was treated with diethyl ether and the product was filtred off to give 1.7 g (45%) of the title compound.

Workup

  1. customthe organic layer was separated
  2. customdried
  3. customevaporated under reduced pressure
  4. additionThe residue was treated with diethyl ether

Sources & evidence

ORD record
ord-80d10fb4fbbf4e17b0dd803562336d9d
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Linked notes

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