Hydrochloric Acid → (Z)-3-(Hex-1-enyl)-N-(3-morpholinopropyl)imidazo[1,2-b]pyridazin-6-amine hydrochloride

HRID 1162111Notes

Reaction equation

HRID 1162111 reaction equation
[C:1]([C:7]1[N:11]2[N:12]=[C:13]([NH:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH:14]=[CH:15][C:10]2=[N:9][CH:8]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].[ClH:26]>C(O)C.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CCOCC>[ClH:26].[CH:1](/[C:7]1[N:11]2[N:12]=[C:13]([NH:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH:14]=[CH:15][C:10]2=[N:9][CH:8]=1)=[CH:2]/[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 2

HCID 313Hydrochloric Acid2×HCID 595195453-(Hex-1-ynyl)-N-(3-morpholinopropyl)imidazo[1,2-b]pyridazin-6-amine

Product 1

HCID 68647862(Z)-3-(Hex-1-enyl)-N-(3-morpholinopropyl)imidazo[1,2-b]pyridazin-6-amine hydrochlorideYield 18%

Reagents, catalysts & solvents 3

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

3-(Hex-1-ynyl)-N-(3-morpholinopropyl)imidazo[1,2-b]pyridazin-6-amine (75 mg, 0.22 mmol) was dissolved in ethanol (4 mL) and Lindlar's catalyst (20 mg) added. After degassing with a nitrogen stream for 10 mins, the reaction was put under a balloon of hydrogen for 48 h. The solids were filtered off and the filtrate was concentrated. The obtained residue was purified by semi-prep HPLC to provide the free-base, which was subsequently converted to the HCl salt with 2N HCl in Et2O to provide the title compound (15 mg, 18%) as an orange solid; 1H NMR (300 MHz, CD3OD) δ 7.67 (d, J=9.6 Hz, 1H), 7.61 (d, J=4.9 Hz, 1H), 6.81-6.74 (m, 2H), 5.88 (dt, J=7.2, 16.2 Hz, 1H), 3.89 (m, 4H), 3.52 (t, J=6.5 Hz, 2H), 3.37-3.22 (m, 6H), 2.44-2.37 (m, 2H), 2.21-2.12 (m, 2H), 1.56-1.39 (m, 4H), 0.95 (t, J=7.1 Hz, 3H); 13C NMR (75 MHz, CD3OD) δ 155.6, 135.0, 127.9, 124.8, 115.8, 114.5, 65.3, 56.8, 53.4, 39.6, 32.6, 30.8, 24.5, 23.6, 14.3 (2 quaternary aromatic carbons did not show); HPLC tR=13.1 min (Synergi), 91.7%; ES-MS: (M+H)=344 m/z.

Workup

  1. customAfter degassing with a nitrogen stream for 10 mins
  2. filtrationThe solids were filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe obtained residue was purified by semi-prep HPLC
  5. customto provide the free-base, which

Sources & evidence

ORD record
ord-b63db71fecd748b9a7c6b8b6fb84f078
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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