Oxalyl chloride → HCID 67976968, compound

HRID 706767Notes

Reaction equation

HRID 706767 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([C:12]([OH:14])=O)=[CH:10][N:11]=2)[CH:8]=1.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:7]4[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]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 552640326-Methoxyimidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 67976968HCID 67976968, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

6-Methoxyimidazo[1,2-a]pyridine-3-carboxylic acid (29.5 mg, 0.154 mmol) was taken up in DCM. Oxalyl chloride (1.1 equivalents) was added followed by a drop of DMF. The reaction was stirred at ambient temperature until bubbling ceased, and then 1-benzyl-1H-indazol-4-amine (34.3 mg, 0.154 mmol) was added followed by DIEA (1.2 equivalents). The reaction was stirred at ambient temperature overnight. The reaction was concentrated, triturated with ether and purified by Preparative TLC (1 mm) eluting with 10% MeOH/DCM to give 15 mg (25%) of the desired product. MS (ES+APCI) m/z=398.3 (M+H).

Workup

  1. customuntil bubbling
  2. stirringThe reaction was stirred at ambient temperature overnight
  3. concentrationThe reaction was concentrated
  4. customtriturated with ether
  5. custompurified by Preparative TLC (1 mm)
  6. washeluting with 10% MeOH/DCM

Sources & evidence

ORD record
ord-6cdec8cbf92b42a2a44ab41d54bd483d
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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