Hydrochloric Acid → (E)-N-(3-Morpholinopropyl)-3-(pent-1-enyl)imidazo[1,2-b]pyridazin-6-amine hydrochloride

HRID 1162106Notes

Reaction equation

HRID 1162106 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.[CH:21](/B(O)O)=[CH:22]\[CH2:23][CH2:24][CH3:25].[ClH:29]>CCOCC>[ClH:29].[O:18]1[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][CH2:12][NH:11][C:8]2[CH:9]=[CH:10][C:5]3[N:6]([C:2](/[CH:21]=[CH:22]/[CH2:23][CH2:24][CH3:25])=[CH:3][N:4]=3)[N:7]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 5702651(1E)-(Pent-1-en-1-yl)boronic acidHCID 686478363-Bromo-N-(3-morpholinopropyl)imidazo[1,2-b]pyridazin-6-amine

Product 1

HCID 68648129(E)-N-(3-Morpholinopropyl)-3-(pent-1-enyl)imidazo[1,2-b]pyridazin-6-amine hydrochlorideYield 55%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Prepared from the product of step A (example 16) and (E)-1-penteneboronic acid according to general procedure 2. The free base was converted to the HCl salt with 2N HCl in Et2O to provide the title compound (58 mg, 55%) as a brown solid; 1H NMR (500 MHz, CD3OD) δ 7.65 (d, J=9.7 Hz, 1H), 7.56 (s, 1H), 6.77-6.63 (m, 3H), 3.91-3.89 (m, 4H), 3.54 (t, J=6.4 Hz, 2H), 3.24-3.21 (m, 6H), 2.27 (q, J=6.8 Hz, 2H), 2.20-2.14 (m, 2H), 1.58-1.51 (m, 2H), 0.98 (t, J=7.4 Hz, 3H); 13C NMR (125 MHz, CD3OD) δ 155.6, 136.8, 134.2, 129.2, 126.4, 124.8, 116.4, 115.0, 65.4, 57.0, 53.5, 39.8, 36.8, 24.4, 23.7, 14.1; HPLC tR=9.3 min (Synergi), 97.3%; ES-MS: (M+H)=330 m/z.

Sources & evidence

ORD record
ord-5eb49804997d49f1a1cb79ec3b6d4a9a
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

Loading…