HCID 86662394, compound → HCID 53237185, compound

HRID 1188721Notes

Reaction equation

HRID 1188721 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)[N:9]=2)=[CH:4][CH:3]=1>C(N)CN>[CH3:27][N:24]1[CH2:25][CH2:26][N:21]([C:18]2[CH:19]=[CH:20][C:15]([NH:14][C:10]3[N:9]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([NH:21][CH2:22][CH2:23][NH2:24])=[N:7][CH:6]=4)[CH:13]=[CH:12][N:11]=3)=[CH:16][CH:17]=2)[CH2:22][CH2:23]1

Participants

3

Reactant 1

HCID 86662394HCID 86662394, compound

Product 1

HCID 53237185HCID 53237185, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 3301EthylenediamineSolvent

Conditions

Temperature
120 °C

Procedure

0.15 g (0.39 mmol) of [4-(6-Chloro-pyridin-3-yl)-pyrimidin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine was dissolved in 2.5 mL ethylenediamine and heated in a sealed tube at 120° C. for 18 h. The reaction was cooled and evaporated to dryness and the crude product was purified by silica gel column chromatography using dichloromethane:methanol:triethylamine (9:1:0.05 to 1:1:0.05) to give the title compound as a pale yellow solid (58 mg, 0.14 mmol, 36%). The product was dissolved in dichloromethane (2 mL) then 0.51 M hydrochloric acid:diethyl ether (0.275 mL, 0.14 mmol) was added, it was stirred for 0.5 h. The mixture was evaporated and the residue was suspended in methanol and filtered to give N-(5-{2-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-pyrimidin-4-yl}-pyridin-2-yl)-ethane-1,2-diamine hydrochloride (35.5 mg, 0.08 mmol, 21%). ESMS m/z 405 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 9.23 (s, 1H), 8.84 (d, J=2.0 Hz, 1H), 8.36 (d, J=5.3 Hz, 1H), 8.15 (dd, J=8.8, 2.3 Hz, 1H), 7.87 (br. S., 3H), 7.62 (d, J=9.3 Hz, 2H), 7.33 (t, J=6.3 Hz, 1H), 7.19 (d, J=5.3 Hz, 1H), 6.91 (d, J=9.3 Hz, 2H), 6.65 (d, J=8.5 Hz, 1H), 3.57 (q, J=6.3 Hz, 2H), 3.05-3.12 (m, 4H), 3.01 (t, J=6.3 Hz, 2H), 2.46-2.49 (m, 4H), 2.25 (s, 3H).

Workup

  1. temperatureThe reaction was cooled
  2. customevaporated to dryness
  3. customthe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d5dd0c2941704df7b1d92f74daf65cca
Source dataset
uspto-grants-2014_03
Patent number
US08674095B2

Reaction notes

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