Hydrochloric Acid → HCID 68648136, compound

HRID 1162112Notes

Reaction equation

HRID 1162112 reaction equation
[C:1]([C:7]1[N:11]2[N:12]=[C:13]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH:14]=[CH:15][C:10]2=[N:9][CH:8]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].[ClH:24]>C(O)C.[Pd].CCOCC>[ClH:24].[CH2:1]([C:7]1[N:11]2[N:12]=[C:13]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH:14]=[CH:15][C:10]2=[N:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 2

HCID 313Hydrochloric Acid2×HCID 59519589HCID 59519589, compound

Product 1

HCID 68648136HCID 68648136, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

3-(Hex-1-ynyl)-N-(pyridin-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amine was dissolved in ethanol (5 mL) with 5% palladium on charcoal and placed under hydrogen (50 psi) in a Parr shaker. After 24 hr, the reaction mixture was filtered through celite and concentrated to provide the free-base. This was converted to the HCl salt with 2N HCl in Et2O to provide the title compound (26 mg, 41%) as an orange solid; 1H NMR (300 MHz, CD3OD) δ 8.52 (d, J=5.0 Hz, 1H), 7.92 (d, J=9.8 Hz, 1H), 7.89-7.83 (dt, J=1.7, 9.4 Hz, 1H), 7.63 (s, 1H), 7.54 (d, J=7.9 Hz, 1H), 7.37-7.35 (m, 1H), 7.31 (d, J=9.8 Hz, 1H), 4.73 (s, 2H), 2.78 (t, J=7.4 Hz, 2H), 1.55-1.48 (m, 2H), 1.29-1.25 (m, 6H), 0.98 (t, J=6.6 Hz, 3H); 13C NMR (75 MHz, CD3OD) δ 158.2, 156.2, 148.8, 139.0, 132.9, 131.9, 123.6, 122.8, 121.0, 119.8, 118.2, 46.9, 32.0, 29.3, 27.1, 23.2, 23.0, 13.8; HPLC tR=9.26 min (Luna), 95.3%; ES-MS: (M+H)=310 m/z.

Workup

  1. filtrationthe reaction mixture was filtered through celite and
  2. concentrationconcentrated
  3. customto provide the free-base

Sources & evidence

ORD record
ord-2e8d809a89284c7f8ecdbabc158f3967
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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