Ammonium Acetate → HCID 178442439, compound

HRID 1881480Notes

Reaction equation

C([O-])(=O)C.[NH4+:5].[C:6]([NH:9][CH:10]([C:32]([NH:34][CH2:35][C:36](=O)[CH2:37][C:38]([CH3:42])([CH3:41])[CH2:39][CH3:40])=O)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[N:20][N:21]([CH3:23])[CH:22]=2)=[CH:14][CH:13]=1)(=[O:8])[CH3:7]>C1(C)C(C)=CC=CC=1>[C:27]([O:26][C:25](=[O:31])[NH:24][C:19]1[C:18]([C:15]2[CH:16]=[CH:17][C:12]([CH2:11][CH:10]([NH:9][C:6](=[O:8])[CH3:7])[C:32]3[NH:34][CH:35]=[C:36]([CH2:37][C:38]([CH3:41])([CH3:42])[CH2:39][CH3:40])[N:5]=3)=[CH:13][CH:14]=2)=[CH:22][N:21]([CH3:23])[N:20]=1)([CH3:29])([CH3:30])[CH3:28]

Participants

Conditions

Temperature: 150 °C

Procedure

Ammonium acetate (1.17 g, 15.2 mmol) was added to an ambient temperature solution of tert-butyl [4-(4-{2-(acetylamino)-3-[(4,4-dimethyl-2-oxohexyl)amino]-3-oxopropyl}phenyl)-1-methyl-1H-pyrazol-3-yl]carbamate (160 mg, 0.30 mmol) in xylene (5 mL). After stirring at 150° C. for 1 h, the reaction mixture was quenched with saturated aqueous sodium bicarbonate and extracted with ethyl acetate and methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% acetone/methylene chloride afforded the title compound. (M+H) found: 509.

Workup

customthe reaction mixture was quenched with saturated aqueous sodium bicarbonate
extractionextracted with ethyl acetate and methylene chloride
dry with materialThe combined organic extracts were dried (magnesium sulfate)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0118fc3a10a14314a20c61d2753ffb47
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318767B2

Reaction notes

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