Hydrochloric Acid → HCID 68648180, compound

HRID 1162115Notes

Reaction equation

HRID 1162115 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.[NH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1.Cl>CCOCC>[ClH:1].[CH2:13]([O:12][CH2:11][C:8]1[N:6]2[N:7]=[C:2]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:3]=[CH:4][C:5]2=[N:10][CH:9]=1)[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 195092-PyridinemethanamineHCID 57470625HCID 57470625, compound

Product 1

HCID 68648180HCID 68648180, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Prepared from 6-chloro-3-(ethoxymethyl)imidazo[1,2-b]pyridazine (8b) and 2-(aminomethyl)pyridine 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, 18%) as a white solid; 1H NMR (500 MHz, CD3OD) δ 8.53-8.52 (m, 1H), 7.90 (d, J=9.7 Hz, 1H), 7.86 (dt, J=1.7, 9.5 Hz, 1H), 7.78 (s, 1H), 7.56 (d, J=9.8 Hz, 1H), 7.38-7.36 (m, 1H), 7.26 (d, J=9.8 Hz, 1H), 4.73 (s, 2H), 4.68 (s, 2H), 3.49 (q, J=7.0 Hz, 2H), 1.10 (t, J=7.1 Hz, 3H); 13C NMR (125 MHz, CD3OD) δ 158.9, 156.6, 149.3, 139.6, 134.7, 128.7, 124.2, 123.6, 123.0, 122.5, 119.9, 67.5, 60.9, 47.4, 15.4; HPLC tR=7.4 min (Luna), 98.5%; ES-MS: (M+H)=284 m/z.

Sources & evidence

ORD record
ord-b8b310a017884c32b9f7a6d0421b5beb
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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