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

HRID 1396371Notes

Reaction equation

HRID 1396371 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]([CH:20]3[CH2:22][CH2:21]3)[N:15]=2)[CH:3]=1.[NH3:23]>>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([NH2:23])=[O:9])=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]3[CH2:22][CH2:21]3)[N:15]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 86689732Ethyl 6-chloro-4-(6-cyclopropylpyridin-2-ylamino)pyridazine-3-carboxylate

Product 1

HCID 866897336-Chloro-4-(6-cyclopropylpyridin-2-ylamino)pyridazine-3-carboxamideYield 88.1%

Procedure

Ethyl 6-chloro-4-(6-cyclopropylpyridin-2-ylamino)pyridazine-3-carboxylate (140 mg, 439 μmol) and ammonia (7M in methanol, 9.44 g, 12 mL, 84.0 mmol) were heated at 50° C. in a sealed tube for 21 h. After cooling to room temperature, concentration in vacuo gave 6-chloro-4-(6-cyclopropylpyridin-2-ylamino)pyridazine-3-carboxamide (112 mg, 88%) as a yellow solid. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 11.51 (br. s., 1H) 9.16 (s, 1H) 8.16 (br. s., 1H) 7.52 (t, J=7.74 Hz, 1H) 6.86-6.96 (m, 1H) 6.68 (d, J=7.93 Hz, 1H) 5.65 (br. s., 1H) 1.99-2.10 (m, 1H) 1.06-1.12 (m, 4H). LCMS (EI/CI) m/z: 290 [M+H]. The crude product was used directly in the next step without further purification.

Workup

  1. concentrationconcentration in vacuo

Sources & evidence

ORD record
ord-cbd04be6a08c437b8cd6e0d4d7bbe222
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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