Ammonia → HCID 86689758, compound

HRID 1396406Notes

Reaction equation

HRID 1396406 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[C:22]3[N:21]=[CH:20][N:19]([CH3:23])[C:18]=3[CH:17]=[CH:16][CH:15]=2)[CH:3]=1.[NH3:24]>>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([NH2:24])=[O:9])=[C:4]([NH:13][C:14]2[C:22]3[N:21]=[CH:20][N:19]([CH3:23])[C:18]=3[CH:17]=[CH:16][CH:15]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 86689757HCID 86689757, compound

Product 1

HCID 86689758HCID 86689758, compoundYield 100%

Procedure

Ethyl 6-chloro-4-(1-methyl-1H-benzo[d]imidazol-4-ylamino)pyridazine-3-carboxylate (285 mg, 859 μmol) 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 solvent was evaporated and the residue dried in high vacuum to give 6-chloro-4-(1-methyl-1H-benzo[d]imidazol-4-ylamino)pyridazine-3-carboxamide (260 mg, 100%) as an off-white solid. 1H NMR (DMSO-d6) δ: 11.36 (s, 1H), 8.74 (s, 1H), 8.22 (s, 1H), 8.09 (s, 1H), 7.41-7.52 (m, 1H), 7.28-7.35 (m, 2H), 7.23 (s, 1H), 3.86 (s, 3H); LC-MS 303.0 [M+H]+.

Workup

  1. customThe flask was sealed
  2. customThe solvent was evaporated
  3. customthe residue dried in high vacuum

Sources & evidence

ORD record
ord-0439bc56c9b246bbb1407998f685e0e7
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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