Hydrochloric Acid → HCID 67342749, compound

HRID 1846653Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([N+:25]([O-])=O)[C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([N:17]3[CH2:23][CH2:22][CH2:21][N:20]([CH3:24])[CH2:19][CH2:18]3)=[O:16])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[OH-].[K+].S(S([O-])=O)([O-])=O.[Na+].[Na+].Cl>O>[NH2:25][C:4]1[C:5]([N:8]2[CH2:9][CH2:10][CH:11]([CH2:14][C:15]([N:17]3[CH2:23][CH2:22][CH2:21][N:20]([CH3:24])[CH2:19][CH2:18]3)=[O:16])[CH2:12][CH2:13]2)=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 0.500 g (1.13 mmol) of 2-(5′-bromo-3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-1-(4-methyl-[1,4]diazepan-1-yl)-ethanone in water (25 mL) is added 1.0 g (17 mmol) of potassium hydroxide followed by 1.2 g (11 mmol) of sodium hydrosulfite. The mixture is heated at 60° C. for 4 hours then cooled to room temperature and the pH of the solution adjusted to neutral by the addition of a 2 N solution of hydrochloric acid. The mixture is extracted with a 3:1 mixture of methylene chloride:isopropanol and the combined organic phase is dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide 0.261 g (56.0%) of 2-(3′-amino-5′-bromo-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-1-(4-methyl-[1,4]diazepan-1-yl)-ethanone.

Workup

temperaturethen cooled to room temperature
extractionThe mixture is extracted with a 3:1 mixture of methylene chloride
dry with materialisopropanol and the combined organic phase is dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-9e0b01582cac4ac789168c51e2151151
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952004B2

Reaction notes

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