Ammonium Chloride → HCID 178439104、化合物

HRID 877374ノート

反応式

HRID 877374 の反応式
[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]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 67165955HCID 67165955、化合物

生成物 1

HCID 178439104HCID 178439104、化合物収率 80%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-19928c21c6ce4c04b5b68efd1d0af8d7
出典データセット
uspto-grants-2015_03
特許番号
US08987310B2

反応ノート

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