N~1~-[2-(Pyrrolidin-1-yl)ethyl]benzene-1,4-diamine → HCID 178426959, compound

HRID 640987Notes

Reaction equation

HRID 640987 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].[N:31]1([CH2:36][CH2:37][NH:38][C:39]2[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=2)[CH2:35][CH2:34][CH2:33][CH2:32]1>C1COCC1>[O:30]=[C:4]1[C:3](=[CH:2][NH:45][C:42]2[CH:43]=[CH:44][C:39]([NH:38][CH2:37][CH2:36][N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:40][CH:41]=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

4

Reactant 2

HCID 16090620N~1~-[2-(Pyrrolidin-1-yl)ethyl]benzene-1,4-diamineHCID 178426964HCID 178426964, compound

Product 1

HCID 178426959HCID 178426959, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 (2.5 mL). To the resulting solution was added N-(2-Pyrrolidin-1-yl-ethyl)-benzene-1,4-diamine (prepared below, 70.8 mg, 0.345 mmol), and the mixture was stirred for 24 h at 65° C. The reaction mixture was cooled to room temperature and then diluted with Hexanes (˜40 mL). The black precipitate that formed was removed by filtration and the filtrate was concentrated in vacuo. The crude residue was dissolved in EtOAc (˜5 mL) and triturated with Hexane (˜50 mL) to give a yellow precipitate. The precipitate was filtered and washed with 0° C. i-prOH (˜5 mL) yielding 25% (0.0366 g, 0.062 mmol) of the title compound.

Workup

  1. customA small screw cap test tube
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customThe black precipitate that formed
  4. customwas removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. dissolutionThe crude residue was dissolved in EtOAc (˜5 mL)
  7. customtriturated with Hexane (˜50 mL)
  8. customto give a yellow precipitate
  9. filtrationThe precipitate was filtered
  10. washwashed with 0° C.

Sources & evidence

ORD record
ord-0a8f9593992242fa9ca6bb7ab36d0fa5
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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