Ammonia → HCID 86689752, compound

HRID 1396425Notes

Reaction equation

HRID 1396425 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([NH:11][C:12]2[CH:17]=[C:16]([Cl:18])[N:15]=[N:14][C:13]=2[C:19]([O:21]CC)=O)[CH:8]=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CO.[NH3:26]>>[C:1]([C:5]1[N:10]=[C:9]([NH:11][C:12]2[CH:17]=[C:16]([Cl:18])[N:15]=[N:14][C:13]=2[C:19]([NH2:26])=[O:21])[CH:8]=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 86689772HCID 86689772, compound

Product 1

HCID 86689752HCID 86689752, compoundYield 99.9%

Procedure

In a 100 mL round bottom flask, ethyl 4-(6-tert-butylpyridin-2-ylamino)-6-chloropyridazine-3-carboxylate (539 mg, 1.61 mmol) was suspended in ammonia 7M in methanol (7.87 g, 10.0 mL, 70.0 mmol). Sealed and stirred at room temperature for 18 h. The solvents were evaporated and the residue dried in high vacuum to give clean 4-(6-tert-butylpyridin-2-ylamino)-6-chloropyridazine-3-carboxamide (492 mg, 99.9% yield) as an off-white solid. 1H NMR (DMSO-d6) δ: 11.94 (s, 1H), 9.23 (s, 1H), 8.84 (s, 1H), 8.19 (s, 1H), 7.74 (t, J=7.9 Hz, 1H), 7.14 (d, J=7.6 Hz, 1H), 6.92 (d, J=7.9 Hz, 1H), 1.34 (s, 9H); LC-MS 306.1, 308.1 [M+H]+.

Workup

  1. customSealed
  2. customThe solvents were evaporated
  3. customthe residue dried in high vacuum

Sources & evidence

ORD record
ord-00b3777174ab4b0b8db1495ebdfceddf
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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