6-Methoxy-3-pyridinylamine → HCID 67318044, compound

HRID 1042794Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.Cl[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:13][N:12]=1>CC(O)CC>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:13][N:12]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A RBF was charged with 6-methoxypyridin-3-amine (155 mg, 1.25 mmol), 1-chloro-4-phenylphthalazine (300 mg, 1.25 mmol), and 2-butanol (4 mL). The vessel was sealed and the mixture was stirred overnight at 90° C. LC/MS shows completion of reaction. Reaction cooled to RT and purified by silica gel chromatography (1-5% MeOH/DCM) to afford N-(6-methoxypyridin-3-yl)-4-phenylphthalazin-1-amine as tan solid. MS [M+H]=329.1. Calc'd for C20H16N4O: 328.4.

Workup

customThe vessel was sealed
customcompletion of reaction
customReaction
temperaturecooled to RT
custompurified by silica gel chromatography (1-5% MeOH/DCM)

Sources & evidence

ORD record: ord-e53d59b7ac634ff8b89ca91114c9793c
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557816B2

Reaction notes

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