Ammonia → HCID 86689816, compound

HRID 1396492Notes

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

Participants

Reactant 3

HCID 222Ammonia

HCID 887Methanol

HCID 86689815HCID 86689815, compound

Product 1

HCID 86689816HCID 86689816, compoundYield 97%

Conditions

Temperature: 40 °C

Procedure

To a solution of give ethyl 6-chloro-4-(6-isopropoxypyridin-2-ylamino)pyridazine-3-carboxylate (530 mg, 1.57 mmol) was added 7N ammonia in MeOH (16.9 mL, 118 mmol). The mixture was stirred at 40° C. for 18 h, after which the solvent was removed to give 6-chloro-4-(6-isopropoxypyridin-2-ylamino)pyridazine-3-carboxamide (470 mg, 97%) as an off-white solid. 1H NMR (400 MHz, CHLOROFORM-d6) δ ppm 11.57 (s, 1H), 9.08 (s, 1H), 8.17 (s, 1H), 7.58 (t, J=7.8 Hz, 1H), 6.50 (d, J=7.3 Hz, 1H), 6.44 (d, J=8.0 Hz, 1H), 5.69 (s, 1H), 5.23 (m, 1H), 1.47 (d, J=6.3 Hz, 6H).

Workup

customafter which the solvent was removed

Sources & evidence

ORD record: ord-dd0f8bac7f604e09b89ead7f1197f6f8
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901124B2

Reaction notes

Loading…