Diisopropylethylamine → HCID 86689757, compound

HRID 1396405Notes

Reaction equation

HRID 1396405 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].Cl.Cl.[CH3:16][N:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[C:25]([NH2:26])[C:20]=2[N:19]=[CH:18]1.CCN(C(C)C)C(C)C>C(#N)C>[Cl:8][C:6]1[N:5]=[N:4][C:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:2]([NH:26][C:25]2[C:20]3[N:19]=[CH:18][N:17]([CH3:16])[C:21]=3[CH:22]=[CH:23][CH:24]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 42614139HCID 42614139, compoundHCID 53428795Ethyl 4,6-dichloropyridazine-3-carboxylate

Product 1

HCID 86689757HCID 86689757, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A heavy walled resealable tube, was charged with ethyl 4,6-dichloropyridazine-3-carboxylate (500 mg, 2.26 mmol) and 1-methyl-1H-benzo[d]imidazol-4-amine dihydrochloride (498 mg, 2.26 mmol) in acetonitrile (3.5 mL) with stirring. DIPEA (877 mg, 1.19 mL, 6.79 mmol) was added and the tube was heated with stirring in an oil bath at 80° C. for 24 h. Solvents evaporated and crude purified by flash chromatography (silica 20-45 μM, 80 g, Thomson, 0 to 20% acetone in dichloromethane, 20 min) to give ethyl 6-chloro-4-(1-methyl-1H-benzo[d]imidazol-4-ylamino)pyridazine-3-carboxylate (461 mg, 1.39 mmol, 61%) as a light yellow solid. 1H NMR (CHLOROFORM-d) δ: 10.42 (s, 1H), 7.92 (s, 1H), 7.30-7.45 (m, 2H), 7.23-7.28 (m, 1H), 7.20 (s, 1H), 4.59 (q, J=7.1 Hz, 2H), 3.91 (s, 3H), 1.51 (t, J=7.2 Hz, 3H); LC-MS 332.0 [M+H]+.

Workup

  1. temperaturethe tube was heated
  2. stirringwith stirring in an oil bath at 80° C. for 24 h
  3. customSolvents evaporated
  4. customcrude purified by flash chromatography (silica 20-45 μM, 80 g, Thomson, 0 to 20% acetone in dichloromethane, 20 min)

Sources & evidence

ORD record
ord-9ec623d1a81440428a5e4bda4a05703b
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

Loading…