Ammonia → 6-Chloro-4-(6-isopropylpyridin-2-ylamino)pyridazine-3-carboxamide

HRID 1396347Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8](OC)=[O:9])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([CH3:21])[CH3:20])[N:14]=2)[CH:3]=1.[NH3:22]>CO>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([NH2:22])=[O:9])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([CH3:21])[CH3:20])[N:14]=2)[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl 6-chloro-4-(6-isopropylpyridin-2-ylamino)pyridazine-3-carboxylate (99 mg, 322 μmol) was added to a pressure tube followed by ammonia (7M in methanol, 3.94 g, 5 mL, 35.0 mmol). The mixture was heated to 50° C. for 18 h, and then additional 7 N ammonia in methanol (7.5 mL) was added. After 24 h, the mixture was cooled, filtered and dried to afford 6-chloro-4-(6-isopropylpyridin-2-ylamino)pyridazine-3-carboxamide (103 mg, 100%) as a yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 11.58 (br. s., 1H) 9.41 (s, 1H) 8.20 (br. s., 1H) 7.60 (t, J=7.83 Hz, 1H) 6.90 (d, J=7.33 Hz, 1H) 6.77 (d, J=8.08 Hz, 1H) 5.72 (br. s., 1H) 3.01-3.16 (m, 1H) 1.37 (d, J=6.82 Hz, 6H). LCMS (EI/CI) m/z: 292 [M+H].

Workup

temperaturethe mixture was cooled
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-18b376aebac34ec383aa62de70c3642c
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901124B2

Reaction notes

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