Tetrahydrofuran → HCID 178426962, compound

HRID 2352867Notes

Reaction equation

HRID 2352867 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>>[O:30]=[C:4]1[C:3](=[CH:2][NH:20][C:16]2[CH:17]=[CH:32][C:33]([O:34][CH2:35][CH2:31][N:5]3[CH2:6][CH2:11][CH2:3][CH2:4]3)=[CH:14][CH:15]=2)[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]1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 178426964HCID 178426964, compound

Product 1

HCID 178426962HCID 178426962, compoundYield 62%

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, 121 mg, 0.298 mmol) and THF (2 mL). To the resulting solution was added 4-(2-Pyrrolidin-1-yl-ethoxy)-phenylamine1 (67.7 mg, 0.329 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature. Hexanes were added to the reaction mixture, and the resulting suspension was filtered. The filtrate then was concentrated in vacuo. The residue was redissolved into EtOAc then diluted with Hexanes causing a precipitate to form. This precipitate was filtered and washed with ˜1 mL of i-prOH yielding 62% (0.109 g, 0.185 mmol) of the title compound.

Workup

  1. customA small screw cap test tube
  2. additionTo the resulting solution was added 4-(2-Pyrrolidin-1-yl-ethoxy)-phenylamine1 (67.7 mg, 0.329 mmol)
  3. temperatureSubsequently, the reaction mixture was cooled to room temperature
  4. filtrationthe resulting suspension was filtered
  5. concentrationThe filtrate then was concentrated in vacuo
  6. dissolutionThe residue was redissolved into EtOAc
  7. additionthen diluted with Hexanes causing a precipitate
  8. customto form
  9. filtrationThis precipitate was filtered

Sources & evidence

ORD record
ord-bcc35713b90441cb8516958a0009f44b
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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