Hydrochloric Acid → HCID 131728395, compound

HRID 1162114Notes

Reaction equation

HRID 1162114 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][O:12][CH2:13][CH3:14])=[CH:9][N:10]=2)[N:7]=1.[O:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][NH2:24])[CH2:17][CH2:16]1.Cl>CCOCC>[ClH:1].[CH2:13]([O:12][CH2:11][C:8]1[N:6]2[N:7]=[C:2]([NH:24][CH2:23][CH2:22][CH2:21][N:18]3[CH2:19][CH2:20][O:15][CH2:16][CH2:17]3)[CH:3]=[CH:4][C:5]2=[N:10][CH:9]=1)[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 61055N-(3-Aminopropyl)morpholineHCID 57470625HCID 57470625, compound

Product 1

HCID 131728395HCID 131728395, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Prepared from 6-chloro-3-(ethoxymethyl)imidazo[1,2-b]pyridazine (8b) 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 (36 mg, 17%) as a white solid; 1H NMR (500 MHz, CD3OD) δ 7.64 (d, J=9.7 Hz, 1H), 7.50 (s, 1H), 6.77 (d, J=9.7 Hz, 1H), 4.80 (s, 2H), 3.90-3.88 (m, 4H), 3.60 (q, J=7.1 Hz, 2H), 3.50 (t, J=6.4 Hz, 2H), 3.26-3.18 (m, 6H), 2.17-2.11 (m, 2H), 1.20 (t, J=7.0 Hz, 3H); 13C NMR (125 MHz, CD3OD) δ 155.6, 137.5, 130.0, 127.0, 125.3, 115.5, 66.7, 65.5, 61.4, 57.0, 53.5, 39.7, 24.6,15.5; HPLC tR=7.7 min (Luna), 97.6%; ES-MS: (M+H)=320 m/z.

Sources & evidence

ORD record
ord-21969bacbd4f4572986e8a8125221fbd
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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