Sodium Hydroxide → 4-(3-(4-(Dimethylamino)benzamido)-2-fluorophenyl)-7-morpholino-9H-pyrido[3,4-b]indole-1-carboxylic acid

HRID 2361356Notes

Reaction equation

HRID 2361356 reaction equation
[CH3:1][N:2]([CH3:43])[C:3]1[CH:42]=[CH:41][C:6]([C:7]([NH:9][C:10]2[C:11]([F:40])=[C:12]([C:16]3[C:28]4[C:27]5[C:22](=[CH:23][C:24]([N:29]6[CH2:34][CH2:33][O:32][CH2:31][CH2:30]6)=[CH:25][CH:26]=5)[NH:21][C:20]=4[C:19]([C:35]([O:37]CC)=[O:36])=[N:18][CH:17]=3)[CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:5][CH:4]=1.[OH-].[Na+]>CO>[CH3:1][N:2]([CH3:43])[C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[C:11]([F:40])=[C:12]([C:16]3[C:28]4[C:27]5[C:22](=[CH:23][C:24]([N:29]6[CH2:30][CH2:31][O:32][CH2:33][CH2:34]6)=[CH:25][CH:26]=5)[NH:21][C:20]=4[C:19]([C:35]([OH:37])=[O:36])=[N:18][CH:17]=3)[CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:41][CH:42]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67994786Ethyl 4-(3-(4-(dimethylamino)benzamido)-2-fluorophenyl)-7-morpholino-9H-pyrido[3,4-b]indole-1-carboxylate

Product 1

HCID 679950664-(3-(4-(Dimethylamino)benzamido)-2-fluorophenyl)-7-morpholino-9H-pyrido[3,4-b]indole-1-carboxylic acidYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of ethyl 4-(3-(4-(dimethylamino)benzamido)-2-fluorophenyl)-7-morpholino-9H-pyrido[3,4-b]indole-1-carboxylate (0.138 g, 0.237 mmol) in methanol (4 mL) at room temperature was added sodium hydroxide (1.068 mL, 1.068 mmol). The mixture was heated at reflux for 45 min. The methanol was removed under vacuum. To the residue was added water (5 mL), and the mixture was acidified with 1 N HCl to pH 5. The insoluble product (0.110 g, 0.199 mmol, 84% yield) was collected as a tan solid with suction filtration and dried at 50° C. under vacuum.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 45 min
  3. customThe methanol was removed under vacuum
  4. additionTo the residue was added water (5 mL)

Sources & evidence

ORD record
ord-563a66d3b3714ab39e79ad6c1b78cff7
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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