Ammonia → HCID 86689801, compound

HRID 1396470Notes

Reaction equation

HRID 1396470 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]=[C:18]([CH3:20])[CH:17]=[C:16]([CH2:21][CH2:22][CH3:23])[N:15]=2)[CH:3]=1.CO.[NH3:26]>>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([NH2:26])=[O:9])=[C:4]([NH:13][C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH2:21][CH2:22][CH3:23])[N:15]=2)[CH:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 86689800Ethyl 6-chloro-4-(4-methyl-6-propylpyridin-2-ylamino)pyridazine-3-carboxylate

Product 1

HCID 86689801HCID 86689801, compoundYield 100%

Conditions

Temperature
40 °C

Procedure

A mixture of ethyl 6-chloro-4-(4-methyl-6-propylpyridin-2-ylamino)pyridazine-3-carboxylate (147 mg, 439 μmol) in ammonia in methanol (7 N, 6.27 mL, 43.9 mmol) was heated to 40° C. for 16 h. The mixture was concentrated in vacuo to give 6-chloro-4-(4-methyl-6-propylpyridin-2-ylamino)pyridazine-3-carboxamide (134 mg, 438 μmol, 100%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.88 (s, 1H), 9.16 (s, 1H), 8.82 (s, 1H), 8.18 (s, 1H), 6.83 (s, 1H), 6.76 (s, 1H), 2.69 (t, J=7.3 Hz, 2H), 2.29 (s, 3H), 1.76 (m, 1H), 0.95 (t, J=7.3 Hz, 3H); MS (EI/CI) m/z: 305.9 [M+H].

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-6aa5bcd95c2f484383815727886d2d13
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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