2-Pyridinemethanamine → 3-chloro-N-(pyridin-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amine

HRID 1162102Notes

Reaction equation

HRID 1162102 reaction equation
[Cl:1][C:2]1[N:6]2[N:7]=[C:8](Cl)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[NH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1>>[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1

Participants

3

Reactant 2

HCID 195092-PyridinemethanamineHCID 152710143,6-Dichloroimidazo[1,2-b]pyridazine

Product 1

HCID 595195873-chloro-N-(pyridin-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amineYield 27%

Procedure

Prepared from 3,6-dichloroimidazo[1,2-b]pyridazine and 2-(aminomethyl)pyridine according to general procedure 3 providing the title compound (56 mg, 27%) as a white solid; 1H NMR (500 MHz, CD3OD) δ 8.50 (d, J=4.9 Hz, 1H), 7.79 (dt, J=1.7, 9.4, Hz, 1H), 7.61 (d, J=9.7 Hz, 1H), 7.54 (d, J=7.9 Hz, 1H), 7.34 (s, 1H), 7.30 (dd, J=5.3, 6.5 Hz, 1H), 6.81 (d, J=9.7 Hz, 1H), 4.68 (s, 1H); 13C NMR (75 MHz, CD3OD) δ 159.7, 155.5, 149.7, 138.7, 127.9, 126.1, 123.7, 123.6, 115.7, 114.6 (one carbon overlapping with solvent); HPLC tR=8.8 min (Synergi), 98.8 %; ES-MS: (M+H)=260 m/z.

Sources & evidence

ORD record
ord-d964cab7bc8947cba91e53629054f09c
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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