Ammonia → HCID 86689813, compound

HRID 1396488Notes

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]([CH:20]([CH3:22])[CH3:21])=[C:16]([O: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]([CH:20]([CH3:22])[CH3:21])=[C:16]([O:23][CH3:24])[N:15]=2)[CH:3]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 887Methanol

HCID 86689812HCID 86689812, compound

Product 1

HCID 86689813HCID 86689813, compoundYield 98%

Conditions

Temperature: 40 °C

Procedure

To a solution of ethyl 6-chloro-4-(5-isopropyl-6-methoxypyridin-2-ylamino)pyridazine-3-carboxylate (500 mg, 1.43 mmol) was added 7N ammonia in MeOH (20.5 mL, 143 mmol). The mixture was stirred at 40° C. for 18 h, after which the solvent was removed to give 6-chloro-4-(5-isopropyl-6-methoxy-pyridin-2-ylamino)-pyridazine-3-carboxylic acid amide (450 mg, 98%) as an off-white solid. 1H NMR (400 MHz, CHLOROFORM-d6) 8 ppm 11.47 (s, 1H), 9.10 (s, 1H), 8.17 (s, 1H), 7.48 (d, J=8.0 Hz, 1H), 6.53 (d, J=7.7 Hz, 1H), 5.71 (s, 1H), 4.04 (s, 3H), 3.18 (m, 1H), 1.23 (d, J=7.1 Hz, 6H).

Workup

customafter which the solvent was removed

Sources & evidence

ORD record: ord-f2b82e09af9040ca8b4c4de9a3c07875
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901124B2

Reaction notes

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