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Dimethylformamide → N-(1-benzyl-5-chloro-3-ethyl-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79267
Notes
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Reaction equation

HRID 79267 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.CN(C)C=O.C(Cl)(=O)C(Cl)=O.[CH2:29]([N:36]1[C:44]2[CH:43]=[CH:42][C:41]([Cl:45])=[C:40]([NH2:46])[C:39]=2[C:38]([CH2:47][CH3:48])=[N:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCl>[CH2:29]([N:36]1[C:44]2[C:39](=[C:40]([NH:46][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])[C:41]([Cl:45])=[CH:42][CH:43]=2)[C:38]([CH2:47][CH3:48])=[N:37]1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 667820257-(2-Methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylic acidHCID 67260717HCID 67260717, compound

Product 1

HCID 53262027N-(1-benzyl-5-chloro-3-ethyl-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamideYield 37.5%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent2×

Procedure

To a magnetically stirred, ice cooled, suspension of 7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylic acid (6.76 mg, 0.0286 mmol) (prepared as in Example 1, steps A-D) in dichloromethane (1 mL) was added N,N-dimethylformamide (1 μL) followed by oxalyl chloride (18.3 μL, 0.0365 mmol; 2M solution in dichloromethane). The mixture was allowed to warm to ambient temperature with occasional venting to allow gases to evolve. After stirring for 30 minutes, 1-benzyl-5-chloro-3-ethyl-1H-indazol-4-amine (8.70 mg, 0.0304 mmol) was added as a solution in dichloromethane (0.5 mL). The mixture was stirred for 60 minutes and then concentrated under reduced pressure. The material was purified using preparative thin layer chromatography on silica, eluting with 5% methanol in dichloromethane to give N-(1-benzyl-5-chloro-3-ethyl-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide (5.4 mg). MS (APCI), positive scan, m/z=504.3 (M+H).

Workup

  1. temperatureice cooled
  2. stirringAfter stirring for 30 minutes
  3. stirringThe mixture was stirred for 60 minutes
  4. concentrationconcentrated under reduced pressure
  5. customThe material was purified
  6. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-cc193fe4154241debc2f2b41b58c51bd
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841455B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes