4-[(2-Pyrrolidin-1-yl-ethylamino)-methyl]-phenylamine → HCID 178426945, compound

HRID 640974Notes

Reaction equation

HRID 640974 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][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([NH2:46])=[CH:42][CH:41]=2)[CH2:35][CH2:34][CH2:33][CH2:32]1>C1COCC1>[O:30]=[C:4]1[C:3](=[CH:2][NH:46][C:43]2[CH:44]=[CH:45][C:40]([CH2:39][NH:38][CH2:37][CH2:36][N:31]3[CH2:32][CH2:33][CH2:34][CH2:35]3)=[CH:41][CH:42]=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 686996624-[(2-Pyrrolidin-1-yl-ethylamino)-methyl]-phenylamineHCID 178426964HCID 178426964, compound

Product 1

HCID 178426945HCID 178426945, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

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, 200 mg, 0.498 mmol) and THF (4 mL). To the resulting solution was added 4-[(2-Pyrrolidin-1-yl-ethylamino)-methyl]-phenylamine (prepared below; 109.2 mg, 0.498 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 ˜5 mL of EtOAc. Hexanes were added causing a yellow precipitate to form. The precipitate was then filtered and washed with ˜1 mL of i-prOH yielding 31% (0.092 g, 0.152 mmol) of the title compound.

Workup

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

Sources & evidence

ORD record
ord-2ba3de4e2ece42eea66a7aaa1188b169
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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