Sodium chloride; water → HCID 89675036, compound

HRID 1396449Notes

Reaction equation

N[C@H]1CCCC[C@H]1N[C:9]1[N:14]=[N:13][C:12]([C:15]([NH2:17])=[O:16])=[C:11]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([CH:27]([CH3:29])[CH3:28])[N:20]=2)[CH:10]=1.N[C@@H]1CCOC[C@@H]1NC(=O)OC(C)(C)C.[Cl-:45].[Na+].O>CN1C(=O)CCC1.C(OCC)(=O)C>[Cl:45][C:9]1[N:14]=[N:13][C:12]([C:15]([NH2:17])=[O:16])=[C:11]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([CH:27]([CH3:29])[CH3:28])[N:20]=2)[CH:10]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 6-chloro-4-(6-isopropyl-5-methoxypyridin-2-ylamino)pyridazine-3-carboxamide (199 mg, 618 μmol, prepared as described in example 32) in NMP (2.06 mL) was added tert-butyl (3R,4R)-4-aminotetrahydro-2H-pyran-3-ylcarbamate (536 mg, 2.47 mmol) in four portions approximately every 12 h and the mixture heated at 140° C. After 48 h total heating time the mixture was cooled and then diluted with ethyl acetate and brine. The phases were separated then the organic phase was washed with brine (2×), then concentrated in vacuo and the residue obtained was purified by chromatography (silica, 10 to 50% methanol in dichloromethane) to give 6-chloro-4-(6-isopropyl-5-methoxypyridin-2-ylamino)pyridazine-3-carboxamide (199 mg, 618 μmol, quantitative) as a light brown solid. MS (EI/CI) m/z: 502.2 [M+H].

Workup

temperatureAfter 48 h total heating time the mixture was cooled
customThe phases were separated
washthe organic phase was washed with brine (2×)
concentrationconcentrated in vacuo
customthe residue obtained
customwas purified by chromatography (silica, 10 to 50% methanol in dichloromethane)

Sources & evidence

ORD record: ord-cbb59d4a9e5b48178224f93362bf32e4
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901124B2

Reaction notes

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