1-(3-Aminopropyl)-4-methylpiperazine → HCID 68857366, compound

HRID 1986302Notes

Reaction equation

HRID 1986302 reaction equation
C(N(C(C)C)CC)(C)C.[NH2:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1.[CH:21]1([NH:24][C:25]([C:27]2[C:35]3[CH:34]=[C:33]([C:36]4[C:41]([Cl:42])=[CH:40][N:39]=[C:38](Cl)[N:37]=4)[S:32][C:31]=3[C:30]([O:44][CH3:45])=[CH:29][CH:28]=2)=[O:26])[CH2:23][CH2:22]1>O1CCOCC1>[CH:21]1([NH:24][C:25]([C:27]2[C:35]3[CH:34]=[C:33]([C:36]4[C:41]([Cl:42])=[CH:40][N:39]=[C:38]([NH:10][CH2:11][CH2:12][CH2:13][N:14]5[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]5)[N:37]=4)[S:32][C:31]=3[C:30]([O:44][CH3:45])=[CH:29][CH:28]=2)=[O:26])[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 81531DiisopropylethylamineHCID 86625353HCID 86625353, compound

Product 1

HCID 68857366HCID 68857366, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Diisopropylethylamine (1.10 mL, 5.78 mmol) and 1-(3-aminopropyl)-4-methylpiperazine (545 mg, 3.47 mmol) are added to a stirred suspension of 2-(2,5-dichloropyrimidin-4-yl)-7-methoxybenzo[b]thiophene-4-carboxylic acid cyclopropylamide (1.14 g, 2.89 mmol) in dry 1,4-dioxane (25 mL) at room temperature. The resultant mixture is heated in an oil bath at 97° C. for 2 days. At room temperature the mixture is filtered off and the solid is washed with MeOH to give the title compound as a solid (600 mg, 33% yield). The filtrate is concentrated and the residue is purified by HLB cartridge eluting with NH4HCO3 (pH=8) in CH3CN 1:0 to 0:1, and then by Stratta® column, eluting with dichloromethane in MeOH 12:1 to 4:1, to give an additional 339 mg of the title compound as a yellow solid. ES+(m/z) 515 (35Cl) and 517 (37Cl) [M+H].

Workup

  1. filtrationAt room temperature the mixture is filtered off
  2. washthe solid is washed with MeOH

Sources & evidence

ORD record
ord-5a4c29fc5b7649cca72b2d0d2a981646
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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