Stannous Chloride → HCID 178461584, compound

HRID 518622Notes

Reaction equation

[CH3:1][C@H:2]1[N:7]([C:8]([C@H:10]2[CH2:15][CH2:14][C@@H:13]([NH:16][C:17]3[C:22]([N+:23]([O-])=O)=[CH:21][N:20]=[C:19]([O:26][CH2:27][CH2:28][N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)[CH:18]=3)[CH2:12][CH2:11]2)=[O:9])[CH2:6][CH2:5][N:4]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:3]1.[Sn](Cl)Cl>CO.CCOC(C)=O>[NH2:23][C:22]1[C:17]([NH:16][C@@H:13]2[CH2:12][CH2:11][C@H:10]([C:8]([N:7]3[CH2:6][CH2:5][N:4]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:3][C@H:2]3[CH3:1])=[O:9])[CH2:15][CH2:14]2)=[CH:18][C:19]([O:26][CH2:27][CH2:28][N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[N:20][CH:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of (R)-tert-butyl 3-methyl-4-(cis-4-(5-nitro-2-(2-(piperidin-1-yl)ethoxy)pyridin-4-ylamino)cyclohexanecarbonyl)piperazine-1-carboxylate (0.2 g, 0.348 mmol) in MeOH (3.48 mL) was added tin(II) chloride (0.264 g, 1.392 mmol). The resulting suspension was stirred at 80° C. for 2 hours. The mixture was cooled to RT, diluted with EtOAc and washed with 1N aqueous NaOH. The organic layer was collected, dried over sodium sulfate and concentrated to afford (R)-tert-butyl 4-(cis-4-(5-amino-2-(2-(piperidin-1-yl)ethoxy)pyridin-4-ylamino)cyclohexanecarbonyl)-3-methylpiperazine-1-carboxylate as a tan solid (190 mg, 100%). MS m/z=545.4 [M+H]. Calc'd for C29H48N6O4: 544.4.

Workup

temperatureThe mixture was cooled to RT
washwashed with 1N aqueous NaOH
customThe organic layer was collected
dry with materialdried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-f19a570faa56402aaa68eb0dd41ca11e
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115127B2

Reaction notes

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