Oxalyl chloride → N-(1-benzyl-1H-indazol-4-yl)-7-(2-morpholinoethoxy)imidazo[1,2-a]pyridine-3-carboxamide

HRID 706664Notes

Reaction equation

HRID 706664 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][N:13]3[C:16]([C:19]([O-:21])=O)=[CH:17][N:18]=[C:12]3[CH:11]=2)[CH2:3][CH2:2]1.[Li+].C(Cl)(=O)C(Cl)=O.[CH2:29]([N:36]1[C:44]2[CH:43]=[CH:42][CH:41]=[C:40]([NH2:45])[C:39]=2[CH:38]=[N:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[CH2:29]([N:36]1[C:44]2[C:39](=[C:40]([NH:45][C:19]([C:16]3[N:13]4[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][N:4]5[CH2:3][CH2:2][O:1][CH2:6][CH2:5]5)=[CH:11][C:12]4=[N:18][CH:17]=3)=[O:21])[CH:41]=[CH:42][CH:43]=2)[CH:38]=[N:37]1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 213273171-benzyl-1H-indazol-4-amineHCID 67261208Lithium 7-(2-morpholinoethoxy)imidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 57384337N-(1-benzyl-1H-indazol-4-yl)-7-(2-morpholinoethoxy)imidazo[1,2-a]pyridine-3-carboxamideYield 12.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of lithium 7-(2-morpholinoethoxy)imidazo[1,2-a]pyridine-3-carboxylate (42 mg, 0.142 mmol) in DCM were added oxalyl chloride (1.1 equivalents) and a drop of DMF. The mixture was stirred until gas evolution stopped. To the reaction mixture were then added 1-benzyl-1H-indazol-4-amine (31.6 mg, 0.142 mmol) and Hunig's base (1.2 equivalents). The reaction was stirred at ambient temperature for two hours and then concentrated. The residue was triturated with diethyl ether followed by chromatographic purification on silica with 10% MeOH/DCM as eluent to provide 8.6 mg of the desired product as a white solid. MS (ES+APCI) m/z=497 (M+H) detected.

Workup

  1. stirringThe reaction was stirred at ambient temperature for two hours
  2. concentrationconcentrated
  3. customThe residue was triturated with diethyl ether
  4. customfollowed by chromatographic purification on silica with 10% MeOH/DCM as eluent

Sources & evidence

ORD record
ord-235f6587fddf42a99d70b111099b9c60
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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