Dimethylformamide → Ammonia methanol

HRID 876894Notes

Reaction equation

HRID 876894 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:12]=[C:13]([CH:19]=[CH:20][CH:21]=3)[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8][CH:9]=2)[NH:4][N:3]=1.ClCCl.[CH3:25][N:26]([CH:28]=O)[CH3:27]>N1C=CC=CC=1>[CH3:14][OH:15].[NH3:1].[CH3:25][N:26]1[CH2:28][CH2:27][N:26]([C:25]2[CH:20]=[CH:19][C:13]([C:14]([NH:1][C:2]3[C:10]4[C:5](=[CH:6][C:7]([C:11]5[CH:12]=[C:13]([CH:19]=[CH:20][CH:21]=5)[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8][CH:9]=4)[NH:4][N:3]=3)=[O:15])=[CH:12][CH:11]=2)[CH2:28][CH2:27]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 67387291HCID 67387291, compound

Product 2

HCID 21705897Ammonia methanolHCID 67387289HCID 67387289, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of ethyl 3-(3-amino-1H-indazol-6-yl)benzoate (160 mg) in 5 mL of pyridine was added the suspension of the above acid chloride in 4 mL of DMF at 0° C. Then the reaction was warmed up to room temperature gradually and stirred overnight. After the reaction was complete as monitored by reverse phase analytical liquid-chromatography electrospray mass spectrometry (LC-MS), 100 mL of dichloromethane was added and the resulting mixture was washed with brine. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica-gel chromatography with dichloromethane: 3.5 N ammonia methanol solution (50:1 v/v) to give the title compound (126 mg), MS m/z: 484.22 (M+1).

Workup

  1. additionwas added
  2. washthe resulting mixture was washed with brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica-gel chromatography with dichloromethane

Sources & evidence

ORD record
ord-74a6075ef76e4733ab62fab71f31360b
Source dataset
uspto-grants-2015_03
Patent number
US08987275B2

Reaction notes

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