N-Ethyl-1-amino-1,3-dimethylbutane → N-(1-benzyl-1H-indazol-4-yl)-6-fluoroimidazo[1,2-a]pyridine-3-carboxamide

HRID 706735Notes

Reaction equation

HRID 706735 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([OH:13])=O)=[CH:9][N:10]=2)[CH:7]=1.C(Cl)(=O)C(Cl)=O.[CH2:20]([N:27]1[C:35]2[CH:34]=[CH:33][CH:32]=[C:31]([NH2:36])[C:30]=2[CH:29]=[N:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(NC(C)CC(C)C)C>ClCCl>[CH2:20]([N:27]1[C:35]2[C:30](=[C:31]([NH:36][C:11]([C:8]3[N:6]4[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]4=[N:10][CH:9]=3)=[O:13])[CH:32]=[CH:33][CH:34]=2)[CH:29]=[N:28]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 39359N-Ethyl-1-amino-1,3-dimethylbutaneHCID 65578Oxalyl chlorideHCID 213273171-benzyl-1H-indazol-4-amineHCID 552681956-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 67976967N-(1-benzyl-1H-indazol-4-yl)-6-fluoroimidazo[1,2-a]pyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid (0.083 g, 0.46 mmol) was added as a suspension to dichloromethane, and then oxalyl dichloride (0.28 mL, 0.55 mmol) was added slowly. The mixture was allowed to stir for 10 minutes, then a solution of 1-benzyl-1H-indazole-4-amine (0.10 g, 0.46 mmol, above, step D) and N-ethyl-isopropylpropan-2-amine (0.11 mL, 0.60 mmol) were added and the reaction stirred for 2 hours. The solvent was concentrated and the resulting crude material was purified on silica gel using ethyl acetate and methanol (Rf=0.18 in 5% MeOH in ethyl acetate) to provide 20 mg of the desired product. MS (ES+APCI) m/z=386.4 (M+H).

Workup

  1. stirringthe reaction stirred for 2 hours
  2. concentrationThe solvent was concentrated
  3. customthe resulting crude material was purified on silica gel

Sources & evidence

ORD record
ord-4990715a7b41466e8c4481b386d40904
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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