Ammonium Chloride → HCID 66818171, compound

HRID 1755055Notes

Reaction equation

O[Li].O.[CH3:4][C:5]1[CH:10]=[C:9]([NH:11][CH3:12])[CH:8]=[C:7]([CH3:13])[C:6]=1/[CH:14]=[CH:15]/[S:16]([N:19]1[CH2:24][CH2:23][C:22]([NH:28][C:29](=O)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]2([CH3:42])[CH2:41][O:40][CH2:39]2)([C:25]([NH2:27])=[O:26])[CH2:21][CH2:20]1)(=[O:18])=[O:17].[Cl-].[NH4+]>C(O)C>[CH3:13][C:7]1[CH:8]=[C:9]([NH:11][CH3:12])[CH:10]=[C:5]([CH3:4])[C:6]=1/[CH:14]=[CH:15]/[S:16]([N:19]1[CH2:24][CH2:23][C:22]2([N:28]=[C:29]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]3([CH3:42])[CH2:39][O:40][CH2:41]3)[NH:27][C:25]2=[O:26])[CH2:21][CH2:20]1)(=[O:17])=[O:18]

Participants

Conditions

Temperature: 50 °C

Procedure

LiOH.H2O (16.6 mg, 0.396 mmol) was added to a solution of 1-[(E)-2-(2,6-dimethyl-4-methylamino-phenyl)-ethenesulfonyl]-4-[9-(3-methyl-oxetan-3-yl)-nonanoylamino]-piperidine-4-carboxylic amide (96 mg, 0.098 mmol) in ethanol (1.0 mL), and the mixture was stirred at 50° C. for two hours. A 50% saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate) to give 8-[(E)-2-(2,6-Dimethyl-4-methylamino-phenyl)-ethenesulfonyl]-2-[8-(3-methyl-oxetan-3-yl)-octyl]-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (54.8 mg, 100%).

Workup

extractionfollowed by extraction with ethyl acetate
dry with materialThe organic layer was then dried over MgSO4
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record: ord-6690fa9249964eb0a907cc9ff80c86aa
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169254B2

Reaction notes

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