Hydrochloric Acid → HCID 86691915, compound

HRID 714463Notes

Reaction equation

N[C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16]([NH:18][CH3:19])=[O:17])[CH:13]=[CH:14][CH:15]=2)[C:5]([C:20]#[N:21])=[C:4]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][OH:31])=[CH:24][CH:23]=2)[C:3]=1[C:32]#[N:33].[ClH:34].N([O-])=O.[Na+]>O>[Cl:34][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16]([NH:18][CH3:19])=[O:17])[CH:13]=[CH:14][CH:15]=2)[C:5]([C:20]#[N:21])=[C:4]([C:22]2[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][OH:31])=[CH:26][CH:27]=2)[C:3]=1[C:32]#[N:33]

Participants

Conditions

Temperature: 0 °C

Procedure

2 g (4.35 mmol) of 3-[({6-amino-3,5-dicyano-4-[4-(2-hydroxyethoxy)phenyl]pyridin-2-yl}-sulfanyl)methyl]-N-methylbenzenecarboxamide Example 8 were dissolved in ice-cooled conc. hydrochloric acid. 0.9 g (13.06 mmol) of sodium nitrite was added, and the mixture was then stirred at 0° C. for 1 h. After 30 min, a barely stirrable solution had formed. 200 ml of water were added to the reaction mixture. The precipitate was filtered off and purified by column chromatography on silica gel 60 (mobile phase: dichloromethane/methanol 50/1→20/1).

Workup

waitAfter 30 min
customa barely stirrable solution had formed
filtrationThe precipitate was filtered off
custompurified by column chromatography on silica gel 60 (mobile phase: dichloromethane/methanol 50/1→20/1)

Sources & evidence

ORD record: ord-ac61e22e08fd4b4ea5f5e90442ca165e
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187428B2

Reaction notes

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