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

HRID 706665Notes

Reaction equation

HRID 706665 reaction equation
CC1(C)[O:6][CH:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][N:12]3[C:15]([C:18]([OH:20])=O)=[CH:16][N:17]=[C:11]3[CH:10]=2)[CH2:4][O:3]1.C(Cl)(=O)C(Cl)=O.[CH2:28]([N:35]1[C:43]2[CH:42]=[CH:41][CH:40]=[C:39]([NH2:44])[C:38]=2[CH:37]=[N:36]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[CH2:28]([N:35]1[C:43]2[C:38](=[C:39]([NH:44][C:18]([C:15]3[N:12]4[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH:5]([OH:6])[CH2:4][OH:3])=[CH:10][C:11]4=[N:17][CH:16]=3)=[O:20])[CH:40]=[CH:41][CH:42]=2)[CH:37]=[N:36]1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 213273171-benzyl-1H-indazol-4-amineHCID 672601837-((2,2-Dimethyl-1,3-dioxolan-4-yl)methoxy)imidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 57384338N-(1-benzyl-1H-indazol-4-yl)-7-(2,3-dihydroxypropoxy)imidazo[1,2-a]pyridine-3-carboxamideYield 14.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A DCM solution of 7-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)imidazo[1,2-a]pyridine-3-carboxylic acid (Example 58, Steps A-C, 109.7 mg, 0.375 mmol) was treated at ambient temperature with oxalyl chloride (1.1 equivalents) and a drop of DMF. After gas evolution ceased, 1-benzyl-1H-indazol-4-amine (83.8 mg, 0.375 mmol) and Hunig's base (1.2 equivalents) were added, and stirring continued overnight. The resulting mixture was concentrated, and triturated with diethyl ether, followed by chromatographic purification on silica with 10% MeOH/DCM as eluent to provide 25.2 mg of the desired product. MS (ES+APCI) m/z=458 (M+H) detected.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. customtriturated with diethyl ether
  3. customfollowed by chromatographic purification on silica with 10% MeOH/DCM as eluent

Sources & evidence

ORD record
ord-04607edac260481bb6b28b5dc256ae65
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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