Hydrochloric Acid → 3-(Hex-1-ynyl)-N-(3-morpholinopropyl)imidazo[1,2-b]pyridazin-6-amine hydrochloride
Reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[ClH:21].CCO[CH2:25][CH3:26]>>[ClH:21].[C:8]([C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1)#[C:9][CH2:10][CH2:5][CH2:25][CH3:26]Participants
4
Procedure
Prepared from the product of step A (example 16) according to general procedure 6. The free base was converted to the HCl salt with 2N HCl in Et2O to provide the title compound (27 mg, 18%) as a brown solid; 1H NMR (500 MHz, CD3OD) δ 7.67 (d, J=9.7 Hz, 1H), 7.60 (s, 1H), 6.83 (d, J=9.7 Hz, 1H), 3.95 (m, 4H), 3.54 (t, J=6.4 Hz, 2H), 3.34-3.24 (m, 6H), 2.56 (t, J=6.4 Hz, 2H), 2.21-2.15 (m, 2H), 1.67-1.54 (m, 4H), 0.99 (t, J=7.4 Hz, 3H); 13C NMR (125 MHz, CD3OD) δ 156.1, 136.6, 132.2, 124.9, 116.5, 115.1, 100.7, 68.1, 65.1, 56.8, 53.4, 39.5, 31.8, 24.3, 23.0, 20.1, 14.0; HPLC tR=12.7 min (Luna), 97.5%; ES-MS: (M+H)=342 m/z.
Sources & evidence
- ORD record
- ord-c4a3b93fe3414395859ca3eccbb72c68
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07820670B2
Reaction notes
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