Ammonia → HCID 86689794, compound

HRID 1396458Notes

Reaction equation

HRID 1396458 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]([C:23]#[N:24])([CH3:22])[CH3:21])[N:15]=2)[CH:3]=1.CO.[NH3:27]>>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([NH2:27])=[O:9])=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([C:23]#[N:24])([CH3:22])[CH3:21])[N:15]=2)[CH:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 866897933-Pyridazinecarboxylic acid, 6-chloro-4-[[6-(1-cyano-1-methylethyl)-2-pyridinyl]amino]-, ethyl ester

Product 1

HCID 86689794HCID 86689794, compoundYield 80.1%

Procedure

In a 50 mL round bottom flask, ethyl 6-chloro-4-(6-(2-cyanopropan-2-yl)pyridin-2-ylamino)pyridazine-3-carboxylate (792 mg, 2.29 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 abundant solid formed during the reaction was separated by filtration, filter cake rinsed with fresh methanol and dried in high vacuum to give clean 6-chloro-4-(6-(2-cyanopropan-2-yl)pyridin-2-ylamino)pyridazine-3-carboxamide (581 mg, 80.1% yield) as an off-white solid. 1H NMR (DMSO-d6) δ: 12.14 (s, 1H), 9.22 (s, 1H), 8.89 (s, 1H), 8.23 (s, 1H), 7.87 (t, J=7.9 Hz, 1H), 7.27 (d, J=7.6 Hz, 1H), 7.10 (d, J=7.9 Hz, 1H), 1.73 (s, 6H); LC-MS 316.9 [M+H]+.

Workup

  1. customSealed
  2. customThe abundant solid formed during the reaction
  3. customwas separated by filtration
  4. filtrationfilter cake
  5. washrinsed with fresh methanol
  6. customdried in high vacuum

Sources & evidence

ORD record
ord-6c1911919f944582bb509516214b6a9b
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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