Hydrochloric Acid → HCID 68647996, compound

HRID 1162113Notes

Reaction equation

HRID 1162113 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][O:12][CH3:13])=[CH:9][N:10]=2)[N:7]=1.[O:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][NH2:23])[CH2:16][CH2:15]1.Cl>CCOCC>[ClH:1].[CH3:13][O:12][CH2:11][C:8]1[N:6]2[N:7]=[C:2]([NH:23][CH2:22][CH2:21][CH2:20][N:17]3[CH2:18][CH2:19][O:14][CH2:15][CH2:16]3)[CH:3]=[CH:4][C:5]2=[N:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 61055N-(3-Aminopropyl)morpholineHCID 57470624HCID 57470624, compound

Product 1

HCID 68647996HCID 68647996, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Prepared from 6-chloro-3-(methoxymethyl)imidazo[1,2-b]pyridazine (8a) and 3-morpholinopropylamine according to general procedure 4 (step B). The free-base was converted to the HCl salt with 2N HCl in Et2O to provide the title compound (35 mg, 31%) as a white solid; 1H NMR (500 MHz, CD3OD) δ 7.67 (d, J=9.8 Hz, 1H), 7.54 (s, 1H), 6.80 (d, J=9.8 Hz, 1H), 4.76 (s, 2H), 3.90-3.89 (m, 4H), 3.51 (t, J=6.5 Hz, 2H), 3.38 (s, 3H), 3.26-3.23 (m, 6H), 2.18-2.13 (m, 2H); 13C NMR (125 MHz, CD3OD) δ 154.7, 136.5, 128.7, 125.7, 124.2, 115.0, 64.3, 62.2, 57.3, 55.9, 52.5, 38.7, 23.6; HPLC tR=8.1 min (Synergi), 95.2%; ES-MS: (M+H)=306 m/z.

Sources & evidence

ORD record
ord-4429449a183142879dfda3255b51d602
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

Loading…