Ammonium Chloride → HCID 178439104, compound

HRID 877374Notes

Reaction equation

[C:1]([CH:3]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[NH:4][C:5](=[O:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:15])[CH3:14])=[CH:9][CH:8]=1)#[N:2].[NH4+].[Cl-].[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C=O)C>[CH:13]([C:10]1[CH:11]=[CH:12][C:7]([CH2:6][C:5]([NH:4][CH:3]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:1]2[NH:27][N:26]=[N:25][N:2]=2)=[O:16])=[CH:8][CH:9]=1)([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution N-[cyano(phenyl)methyl]-2-(4-isopropylphenyl)acetamide (58.0 mg, 0.198 mmol) in 0.5 ml of anhydrous DMF was added NH4Cl (12.0 mg, 0.218 mmol) and NaN3 (14.00 mg, 0.218 mmol). The resulting solution was stirred at 110° C. for 16 hour. Filtered and the filtrate was purified by preparative HPLC (5-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column) to afford 53.0 mg (80%) of the title compound. 1H NMR (CD3OD, 400 MHz) δ 7.326 (m, 5H), 7.169 (ABq, J=8.2 Hz, 4H), 6.460 (s, 1H), 3.583 (ABq, J=14.5 Hz, 2H), 2.856 (sept, J=7.0 Hz, 1H), 1.214 (d, J=7.0 Hz, 6H). ES-MS [M+1]+: 336.2.

Workup

filtrationFiltered
customthe filtrate was purified by preparative HPLC (5-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column)

Sources & evidence

ORD record: ord-19928c21c6ce4c04b5b68efd1d0af8d7
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987310B2

Reaction notes

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