Ammonia → HCID 86689755, compound

HRID 1396402Notes

Reaction equation

HRID 1396402 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]3[CH2:22][CH2:21][CH2:20]3)[N:14]=2)[CH:3]=1.CO.[NH3:25]>>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([NH2:25])=[O:9])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]3[CH2:22][CH2:21][CH2:20]3)[N:14]=2)[CH:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 86689754HCID 86689754, compound

Product 1

HCID 86689755HCID 86689755, compoundYield 84.3%

Procedure

In a 100 mL round bottom flask, methyl 6-chloro-4-(6-cyclobutylpyridin-2-ylamino)pyridazine-3-carboxylate (350 mg, 1.1 mmol) was suspended in ammonia 7M in methanol (7.87 g, 10.0 mL, 70.0 mmol). The flask was sealed and stirred at room temperature for 18 h. The solid formed was separated by filtration and dried in high vacuum to give 6-chloro-4-(6-cyclobutylpyridin-2-ylamino)pyridazine-3-carboxamide (281 mg, 84.3% yield) as a white solid. 1H NMR (DMSO-d6) δ: 11.95 (s, 1H), 9.34 (s, 1H), 8.85 (s, 1H), 8.20 (s, 1H), 7.69 (t, J=7.7 Hz, 1H), 6.91 (dd, J=7.7, 3.6 Hz, 2H), 3.66 (quin, J=8.6 Hz, 1H), 2.19-2.40 (m, 4H), 1.78-2.15 (m, 2H); LC-MS 304.1 [M+H]+.

Workup

  1. customThe flask was sealed
  2. customThe solid formed
  3. customwas separated by filtration
  4. customdried in high vacuum

Sources & evidence

ORD record
ord-770d06d1546d47328bf6f4d0c29e9685
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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