1-(3-Aminopropyl)-4-methylpiperazine → 2-{5-Methyl-2-[3-(4-methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-6-sulfonic acid benzhydryl-amide

HRID 1986207Notes

Reaction equation

[CH:1]([NH:14][S:15]([C:18]1[CH:19]=[CH:20][C:21]2[CH:25]=[C:24]([C:26]3[C:31]([CH3:32])=[CH:30][N:29]=[C:28](Cl)[N:27]=3)[S:23][C:22]=2[CH:34]=1)(=[O:17])=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[NH2:44][CH2:45][CH2:46][CH2:47][N:48]1[CH2:53][CH2:52][N:51]([CH3:54])[CH2:50][CH2:49]1>O1CCOCC1>[CH:1]([NH:14][S:15]([C:18]1[CH:19]=[CH:20][C:21]2[CH:25]=[C:24]([C:26]3[C:31]([CH3:32])=[CH:30][N:29]=[C:28]([NH:44][CH2:45][CH2:46][CH2:47][N:48]4[CH2:49][CH2:50][N:51]([CH3:54])[CH2:52][CH2:53]4)[N:27]=3)[S:23][C:22]=2[CH:34]=1)(=[O:17])=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 97 °C

Procedure

To a stirred suspension of 2-(2-chloro-5-methylpyrimidin-4-yl)-benzo[b]thiophene-6-sulfonic acid benzhydrylamide (457 mg, 0.903 mmol) in dry 1,4-dioxane (4.5 mL) is added diisopropylethylamine (0.315 mL, 1.81 mmol) and 1-(3-aminopropyl)-4-methylpiperazine (213 mg, 1.35 mmol). The mixture is heated at 97° C. for 1 day. After concentration and subsequent chromatographic purification on silica gel, eluting with 2 M NH3/MeOH in dichloromethane: 0-10%, the title compound is obtained as a yellow solid (317 mg, 57% yield). ES+(m/z) 627 [M+H].

Workup

concentrationAfter concentration and subsequent chromatographic purification on silica gel
washeluting with 2 M NH3/MeOH in dichloromethane

Sources & evidence

ORD record: ord-4a2623fd4c16422d8fc7962b616cf0d3
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547691B2

Reaction notes

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