Oxalyl chloride → HCID 67990391, compound

HRID 706757Notes

Reaction equation

HRID 706757 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]([OH:17])=O)=[CH:13][N:14]=[C:8]2[CH:7]=1.C(Cl)(=O)C(Cl)=O.[CH2:24]([N:31]1[C:39]2[CH:38]=[CH:37][CH:36]=[C:35]([NH2:40])[C:34]=2[CH:33]=[N:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C=O)C>[CH2:24]([N:31]1[C:39]2[C:34](=[C:35]([NH:40][C:15]([C:12]3[N:9]4[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:7][C:8]4=[N:14][CH:13]=3)=[O:17])[CH:36]=[CH:37][CH:38]=2)[CH:33]=[N:32]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 213273171-benzyl-1H-indazol-4-amineHCID 667820257-(2-Methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 67990391HCID 67990391, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylic acid (50 mg; 0.21 mmol) in methylene chloride (2 mL) was added a catalytic (0.005 mL) amount of DMF followed by oxalyl chloride (0.23 mmol; 2M solution in methylene chloride). The mixture was stirred in a sealed vial until effervescence ceased (approximately 30 minutes), with occasional venting to release gas. 1-Benzyl-1H-indazol-4-amine (Example 155, Steps A-B; 47 mg; 0.21 mmol) was added as a solution in methylene chloride (1 mL) followed by diisopropylethylamine (33 mg; 0.25 mmol). The mixture was stirred for 16 hours at ambient temperature, during which time a suspension formed. The mixture was partitioned between water and methylene chloride and the suspension was extracted multiple times with methylene chloride. The combined organic phases (which contained suspended solids) were concentrated under reduced pressure. The resulting solid material was triturated with ether and collected by filtration. The solids were washed with ether, water and then ether again. The material was dried under vacuum to give an off white solid (67 mg). MS (APCI), m/z=442.2 (M+H).

Workup

  1. custom(approximately 30 minutes)
  2. stirringThe mixture was stirred for 16 hours at ambient temperature, during which time a suspension
  3. customformed
  4. customThe mixture was partitioned between water and methylene chloride
  5. extractionthe suspension was extracted multiple times with methylene chloride
  6. concentrationThe combined organic phases (which contained suspended solids) were concentrated under reduced pressure
  7. customThe resulting solid material was triturated with ether
  8. filtrationcollected by filtration
  9. washThe solids were washed with ether, water
  10. customThe material was dried under vacuum

Sources & evidence

ORD record
ord-395fa8c1ed394ff6b4e3298032e0ec35
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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