Oxalyl chloride → HCID 67976961, compound

HRID 706747Notes

Reaction equation

HRID 706747 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:12]([OH:14])=O)=[CH:10][N:11]=[C:5]2[CH:4]=1)#[N:2].C(Cl)(=O)C(Cl)=O.[CH2:21]([N:28]1[C:36]2[CH:35]=[CH:34][CH:33]=[C:32]([NH2:37])[C:31]=2[CH:30]=[N:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[CH2:21]([N:28]1[C:36]2[C:31](=[C:32]([NH:37][C:12]([C:9]3[N:6]4[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]4=[N:11][CH:10]=3)=[O:14])[CH:33]=[CH:34][CH:35]=2)[CH:30]=[N:29]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 213273171-benzyl-1H-indazol-4-amineHCID 55265823HCID 55265823, compound

Product 1

HCID 67976961HCID 67976961, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-cyanoimidazo[1,2-a]pyridine-3-carboxylic acid (0.0527 g, 0.282 mmol) in 0.200 mL of CH2Cl2 was added a drop of DMF followed by oxalyl chloride (1.1 equivalents, 2M CH2Cl2). The reaction was stirred for 5 minutes until bubbling ceased. 1-Benzyl-1H-indazol-4-amine (0.0629 g, 0.282 mmol) was added as a solution in 0.600 mL of CH2Cl2 followed by DIEA (1.2 equivalents). The reaction was stirred at ambient temperature overnight. The reaction was concentrated and the solids were washed with Et2O, water, 2M Na2CO3, water, and finally with Et2O again to provided the desired product as a beige solid 0.072 g (65%). MS (ES+APCI) m/z=393 (M+H).

Workup

  1. customuntil bubbling
  2. stirringThe reaction was stirred at ambient temperature overnight
  3. concentrationThe reaction was concentrated
  4. washthe solids were washed with Et2O, water, 2M Na2CO3, water

Sources & evidence

ORD record
ord-e5640c4e8e1d489e8fcd67288f15b421
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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