Diisopropylethylamine → 2-{4-[Bis-(1-pyridin-2-yl-ethyl)-amino]-butyl}-isoindole-1,3-dione

HRID 251095

Reaction equation

HRID 251095 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7](OS(C)(=O)=O)[CH3:8].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]1[C:35](=[O:36])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]1=[O:37])[CH3:21].CCN(C(C)C)C(C)C>CC#N.CN(C1C=CN=CC=1)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([N:22]([CH:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=1)[CH3:21])[CH2:23][CH2:24][CH2:25][CH2:26][N:27]1[C:35](=[O:36])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]1=[O:37])[CH3:8]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 57655977HCID 57655977, compoundHCID 589971132-[4-(1-Pyridin-2-yl-ethylamino)-butyl]-isoindole-1,3-dione

Product 1

HCID 672717472-{4-[Bis-(1-pyridin-2-yl-ethyl)-amino]-butyl}-isoindole-1,3-dione

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Using General Procedure A: To a stirred solution of methanesulphonic acid 1-pyridin-2-yl-ethyl ester (269 mg, 1.34 mmol) and 2-[4-(1-pyridin-2-yl-ethylamino)-butyl]-isoindole-1,3-dione (356 mg, 1.10 mmol) in CH3CN (5 mL) at room temperature was added DIPEA (0.30 mL, 1.72 mmol) and KI (13 mg, 0.078 mmol). After 3 hours the temperature was increased to 60° C. and the mixture stirred for another 17 hours. KI (23 mg, 0.139 mmol) and DMAP (35 mg, 0.286 mmol) were added and the reaction stirred for a further 2 hours. Work up and purification by flash chromatography (35:1:1 CH2Cl2:MeOH:NH4OH) afforded pure 2-{4-[bis-(1-pyridin-2-yl-ethyl)-amino]-butyl}-isoindole-1,3-dione as a mixture of diastereomers (139 mg, 30%). 1H NMR (CDCl3) δ 1.18-1.49 (m, 10H) containing 1.27 (d, 3H, J=7.0 Hz) and 1.42 (d, 3H, J=7.1 Hz), 2.51-2.80 (m, 2H), 3.44-3.52 (m, 2H), 4.03-4.12 (m, 2H), 6.98-7.07 (m, 2H), 7.31 (d, 1H, J=7.9 Hz), 7.45-7.61 (m, 3H) containing 7.47 (d, 1H, J=7.9 Hz), 7.66-7.70 (m, 2H), 7.76-7.81 (m, 2H), 8.43-8.48 (m, 2H). ES-MS m/z 429 [M+H].

Workup

  1. stirringthe reaction stirred for a further 2 hours
  2. customWork up and purification by flash chromatography (35:1:1 CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-cee9213c62ed4c7fbe26bbf69e89d742
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Linked notes

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