Stannous Chloride → HCID 178457857, compound

HRID 518646Notes

Reaction equation

[CH:1]([NH:4][C:5]([C@H:7]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]2[C:19]([N+:20]([O-])=O)=[CH:18][N:17]=[C:16]([O:23][CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[CH:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[Sn](Cl)Cl>CO>[NH2:20][C:19]1[C:14]([NH:13][C@@H:10]2[CH2:9][CH2:8][C@H:7]([C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])[CH2:12][CH2:11]2)=[CH:15][C:16]([O:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[N:17][CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of cis-N-isopropyl-4-(5-nitro-2-(2-(piperidin-1-yl)ethoxy)pyridin-4-ylamino)cyclohexanecarboxamide (10.79 g, 24.89 mmol) in MeOH (124 mL) was added tin (II) chloride (18.88 g, 100 mmol), and the reaction was stirred at 80° C. for 2 hours. The reaction mixture was concentrated in vacuo, and the residue was dissolved in EtOAc, then diluted with 1N aqueous NaOH. The layers were separated, and the organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to yield cis-4-(5-amino-2-(2-(piperidin-1-yl)ethoxy)pyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide (8.06 g, 80% yield). MS m/z=404.2 [M+H], calc 403.56 for C22H37N5O2.

Workup

concentrationThe reaction mixture was concentrated in vacuo
dissolutionthe residue was dissolved in EtOAc
additiondiluted with 1N aqueous NaOH
customThe layers were separated
washthe organic layer was washed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9bb5b97ed4464e5986c0cacbd0582c76
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115127B2

Reaction notes

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