Oxalyl chloride → HCID 67976237, compound

HRID 706749Notes

Reaction equation

HRID 706749 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][N:14]3[C:17]([C:20]([O-:22])=O)=[CH:18][N:19]=[C:13]3[CH:12]=2)[CH2:4][CH2:3]1.[Li+].C(Cl)(=O)C(Cl)=O.[CH2:30]([N:37]1[C:45]2[CH:44]=[CH:43][CH:42]=[C:41]([NH2:46])[C:40]=2[CH:39]=[N:38]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[CH2:30]([N:37]1[C:45]2[C:40](=[C:41]([NH:46][C:20]([C:17]3[N:14]4[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][N:5]5[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]5)=[CH:12][C:13]4=[N:19][CH:18]=3)=[O:22])[CH:42]=[CH:43][CH:44]=2)[CH:39]=[N:38]1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 213273171-benzyl-1H-indazol-4-amineHCID 67252742Lithium 7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 67976237HCID 67976237, compoundYield 7.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of lithium 7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxylate (0.0585 g, 0.189 mmol) in CH2Cl2 was added a drop of DMF. Oxalyl chloride (1.1 equivalents, 2M CH2Cl2) was added and the reaction stirred at ambient temperature until bubbling ceased (about 5 minutes). 1-Benzyl-1H-indazol-4-amine (0.042 g, 0.189 mmol) was added followed by DIEA (1.2 equivalents). The reaction was stirred at ambient temperature for 4 hours. The reaction was concentrated and washed with Et2O, water, and finally with Et2O again. The pale yellow solid was dried, providing 0.027 g of crude product. The crude material was purified using reverse phase chromatography eluting with a gradient of 0 to 90% ACN/water to give 0.007 g (7%) of the desired product. MS (ES+APCI) m/z=510 (M+H).

Workup

  1. customuntil bubbling
  2. custom(about 5 minutes)
  3. stirringThe reaction was stirred at ambient temperature for 4 hours
  4. concentrationThe reaction was concentrated
  5. washwashed with Et2O, water
  6. customThe pale yellow solid was dried
  7. customproviding 0.027 g of crude product
  8. customThe crude material was purified
  9. washeluting with a gradient of 0 to 90% ACN/water

Sources & evidence

ORD record
ord-aa5024f31a3d4e92a8f84ea8cd59824f
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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