Ammonia → HCID 86689798, compound

HRID 1396464Notes

Reaction equation

HRID 1396464 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]([C:20]([OH:23])([CH3:22])[CH3:21])[N:15]=2)[CH:3]=1.CO.[NH3:26]>>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([NH2:26])=[O:9])=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([OH:23])([CH3:22])[CH3:21])[N:15]=2)[CH:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 86689797HCID 86689797, compound

Product 1

HCID 86689798HCID 86689798, compoundYield 33.3%

Procedure

In a 50 mL round bottom flask, ethyl 6-chloro-4-(6-(2-hydroxypropan-2-yl)pyridin-2-ylamino)pyridazine-3-carboxylate (792 mg, 2.35 mmol) was suspended in ammonia 7M in methanol (7.87 g, 10.0 mL, 70.0 mmol). Sealed and stirred at room temperature for 5 h. The solvents were evaporated and the residue purified by flash chromatography (spherical silica 20-45 μM, 50 g, Versaflash Supelco) eluting with 0 to 5% over 20 min (MeOH containing 10% NH4OH)/CH2Cl2 to give 6-chloro-4-(6-(2-hydroxypropan-2-yl)pyridin-2-ylamino)pyridazine-3-carboxamide (241 mg, 33.3% yield) as an off-white solid. 1H NMR (CHLOROFORM-d) δ: 11.64 (s, 1H), 8.96 (s, 1H), 8.18 (br. s., 1H), 7.71 (t, J=7.9 Hz, 1H), 7.25 (d, J=7.6 Hz, 1H), 6.86 (d, J=8.3 Hz, 1H), 5.70 (br. s., 1H), 1.64 (s, 6H); LC-MS 308.0, 310.0 [M+H]+.

Workup

  1. customSealed
  2. customThe solvents were evaporated
  3. customthe residue purified by flash chromatography (spherical silica 20-45 μM, 50 g, Versaflash Supelco)
  4. washeluting with 0 to 5% over 20 min (MeOH containing 10% NH4OH)/CH2Cl2

Sources & evidence

ORD record
ord-3708b2381c82488d941861b5a978adb1
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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