Tetrahydrofuran → HCID 178464083, compound

HRID 640947Notes

Reaction equation

HRID 640947 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].[CH2:31]1[CH2:35][O:34][CH2:33][CH2:32]1>>[CH2:16]([N:20]([CH2:21][CH3:23])[CH2:31][CH2:35][O:34][C:33]1[CH:32]=[CH:11][C:6]([NH:5][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:7][CH:8]=1)[CH3:15]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 178426964HCID 178426964, compound

Product 1

HCID 178464083HCID 178464083, compoundYield 8.8%

Conditions

Temperature
65 °C

Procedure

A small screw cap 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-Diethylamino-ethoxy)-phenylamine1 (51.7 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. The filtrate was then concentrated in vacuo and then redissolved into EtOAc and then Hexanes were added causing a precipitate to form. The precipitate was then filtered and washed with ˜1 mL of i-prOH yielding 8.8% (0.013 g, 0.022 mmol) of the title compound.

Workup

  1. customA small screw cap test tube
  2. additionTo the resulting solution was added 4-(2-Diethylamino-ethoxy)-phenylamine1 (51.7 mg, 0.249 mmol)
  3. temperatureThe reaction mixture was cooled to room temperature
  4. concentrationThe filtrate was then concentrated in vacuo
  5. dissolutionredissolved into EtOAc
  6. additionHexanes were added
  7. customto form
  8. filtrationThe precipitate was then filtered

Sources & evidence

ORD record
ord-3a0883bf0fa841ea8718ff9c2313ad72
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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