Water → 6-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]pyridazine-3-carboxamide

HRID 1455949Notes

Reaction equation

Cl.[CH2:2]([NH:4][CH2:5][C:6]1[CH:11]=[C:10]([Br:12])[CH:9]=[CH:8][C:7]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:3].Cl[C:22]1[N:27]=[N:26][C:25]([C:28]([NH2:30])=[O:29])=[CH:24][CH:23]=1.C([O-])(O)=O.[Na+].O>CN1CCCC1=O.C(OCC)(=O)C>[CH2:14]([O:13][C:7]1[CH:8]=[CH:9][C:10]([Br:12])=[CH:11][C:6]=1[CH2:5][N:4]([C:22]1[N:27]=[N:26][C:25]([C:28]([NH2:30])=[O:29])=[CH:24][CH:23]=1)[CH2:2][CH3:3])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 115 °C

Procedure

A mixture of N-ethyl-N-(2-benzyloxy-5-bromobenzyl)amine hydrochloride salt (87 g), 6-chloropyridazine-3-carboxamide (35 g) and NaHCO3 (41 g) in 1-methyl-2-pyrrolidinone was heated at 115° C. for 24 hours, cooled to 20° C. and added to water (1100 ml) with vigorous stirring, maintaining the temperature below 30° C. with external cooling. Ethyl acetate (725 ml) was added and the mixture stirred at 20° C. for 2 hours. The precipitate was filtered, dried, washed with 40-60 petroleum ether and dried under vacuum at 65° C. to give 6-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]pyridazine-3-carboxamide (83 g, 84.7% yield), mpt. 171°-172° C.

Workup

temperaturecooled to 20° C.
temperaturemaintaining the temperature below 30° C. with external cooling
filtrationThe precipitate was filtered
customdried
washwashed with 40-60 petroleum ether
customdried under vacuum at 65° C.

Sources & evidence

ORD record: ord-2305036eabc34346af9dd7f6acb12d48
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05843942

Reaction notes

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