4-(2-Dimethylaminoethyl)aniline → HCID 178426938, compound

HRID 640971Notes

Reaction equation

HRID 640971 reaction equation
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[N:24]([CH3:29])[N:25]=[C:26]([CH3:28])[CH:27]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:30].[CH3:31][N:32]([CH3:42])[CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([NH2:41])=[CH:37][CH:36]=1>C1COCC1>[CH3:42][N:32]([CH3:31])[CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([NH:41][CH:2]=[C:3]2[C:11]3[C:6](=[CH:7][C:8]([C:12]([C:14]4[CH:15]=[C:16]([NH:20][C:21]([C:23]5[N:24]([CH3:29])[N:25]=[C:26]([CH3:28])[CH:27]=5)=[O:22])[CH:17]=[CH:18][CH:19]=4)=[O:13])=[CH:9][CH:10]=3)[NH:5][C:4]2=[O:30])=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 149398614-(2-Dimethylaminoethyl)anilineHCID 178426964HCID 178426964, compound

Product 1

HCID 178426938HCID 178426938, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

test tube was charged with 2,5-Dimethyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 60, 100 mg, 0.249 mmol) and THF (2 mL). To the resulting solution was added 4-(2-Dimethylamino-ethyl)-phenylamine (40.9 mg, 0.249 mmol), and the mixture was stirred for 24 h at 65° C. The reaction mixture was cooled to room temperature. Hexanes were added to the reaction mixture causing a black precipitate to form. The precipitate was vacuum filtered and the filtrate was then concentrated in vacuo and redissolved into ˜3 mL of EtOAc. Hexanes were added causing a light brown precipitate to form. The precipitate was then filtered and washed with ˜1 mL of i-prOH yielding 12% (0.016 g, 0.029 mmol) of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customto form
  3. filtrationfiltered
  4. concentrationthe filtrate was then concentrated in vacuo
  5. dissolutionredissolved into ˜3 mL of EtOAc
  6. additionHexanes were added
  7. customto form
  8. filtrationThe precipitate was then filtered

Sources & evidence

ORD record
ord-5e53944cd7544068a9b88efa676ee02c
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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