Ammonia → HCID 86689780, compound

HRID 1396436Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8](OCC)=[O:9])=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([CH2:22][CH2:23][CH3:24])[N:15]=2)[CH:3]=1.[NH3:25]>CO>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([NH2:25])=[O:9])=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([CH2:22][CH2:23][CH3:24])[N:15]=2)[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of ethyl 6-chloro-4-(5-methoxy-6-propylpyridin-2-ylamino)pyridazine-3-carboxylate (1.22 g, 3.48 mmol) in methanol (10 mL) was added 7 N ammonia in methanol (23.6 g, 30 mL, 210 mmol) and the mixture stirred at 50° C. in a sealed tube for 16 h. The mixture was concentrated in vacuo to give 6-chloro-4-(5-methoxy-6-propylpyridin-2-ylamino)pyridazine-3-carboxamide (1.113 g, 3.46 mmol, 100%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.72 (s, 1H), 8.89 (s, 1H), 8.77 (s, 1H), 8.13 (s, 1H), 7.47 (d, J=8.6 Hz, 1H), 7.01 (d, J=8.6 Hz, 1H), 3.81 (s, 3H), 2.74 (t, J=7.3 Hz, 2H), 1.75 (m, 2H), 0.97 (t, J=7.3 Hz, 3H); MS (EI/CI) m/z: 321.9 [M+H].

Workup

concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-eb792307aa8b412cb8881475250f914d
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901124B2

Reaction notes

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