Dimethylformamide → 6-[N-(5-Chloro-2-(cyclopropylmethoxy)benzyl)-N-ethylamino]pyridazine-3-carboxamide

HRID 1604359Notes

Reaction equation

HRID 1604359 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[O:12][CH2:13][CH:14]1[CH2:16][CH2:15]1)[CH3:2].Cl[C:18]1[N:23]=[N:22][C:21]([C:24]([NH2:26])=[O:25])=[CH:20][CH:19]=1.C(N(C(C)C)CC)(C)C.CN(C=O)C>O>[Cl:11][C:9]1[CH:8]=[CH:7][C:6]([O:12][CH2:13][CH:14]2[CH2:15][CH2:16]2)=[C:5]([CH:10]=1)[CH2:4][N:3]([C:18]1[N:23]=[N:22][C:21]([C:24]([NH2:26])=[O:25])=[CH:20][CH:19]=1)[CH2:1][CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 125775576-Chloropyridazine-3-carboxamideHCID 22622510N-ethyl-5-chloro-2-(cyclopropylmethoxy)benzylamine

Product 1

HCID 226224936-[N-(5-Chloro-2-(cyclopropylmethoxy)benzyl)-N-ethylamino]pyridazine-3-carboxamideYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-ethyl-5-chloro-2-(cyclopropylmethoxy)benzylamine (reference example 20) (4.4 g, 18.4 mmol), 6-chloropyridazine-3-carboxamide (3.0 g 19 mmol), di-isopropylethylamine (5.0 ml, 29 mmol) and DMF (25 ml) was stirred at reflux for 16 hours. The mixture was cooled and diluted with water (50 ml), the gum was allowed to settle out and the supernatant liquor decanted. The gum was dissolved in dichloromethane and stirred while adding 2N hydrochloric acid (50 ml). A precipitate formed after 10 minutes. The solid was filtered off and washed with dichloromethane (10 ml) and ether (20 ml) to give a buff solid (3.8 g, 61%) m.p. 177-8° C.

Workup

  1. temperatureat reflux for 16 hours
  2. temperatureThe mixture was cooled
  3. customthe supernatant liquor decanted
  4. dissolutionThe gum was dissolved in dichloromethane
  5. stirringstirred
  6. additionwhile adding 2N hydrochloric acid (50 ml)
  7. customA precipitate formed after 10 minutes
  8. filtrationThe solid was filtered off
  9. washwashed with dichloromethane (10 ml) and ether (20 ml)

Sources & evidence

ORD record
ord-15f7f0e0bf434a55a1327429628d0467
Source dataset
uspto-grants-1999_11
Patent number
US05994353

Reaction notes

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