Methyl iodide → HCID 67545272、化合物

HRID 1256545ノート

反応式

HRID 1256545 の反応式
[H-].[Na+].[F:3][CH:4]([F:42])[C:5]1[N:9]([C:10]2[N:15]=[C:14]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[N:13]=[C:12]([C:22]3[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:24][CH:23]=3)[N:11]=2)[C:8]2[CH:36]=[CH:37][CH:38]=[C:39]([O:40][CH3:41])[C:7]=2[N:6]=1.I[CH3:44]>CN(C=O)C.O>[F:42][CH:4]([F:3])[C:5]1[N:9]([C:10]2[N:15]=[C:14]([N:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[N:13]=[C:12]([C:22]3[CH:23]=[CH:24][C:25]([N:28]([CH3:44])[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:26][CH:27]=3)[N:11]=2)[C:8]2[CH:36]=[CH:37][CH:38]=[C:39]([O:40][CH3:41])[C:7]=2[N:6]=1

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53488103tert-Butyl (4-{4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(morpholin-4-yl)-1,3,5-triazin-2-yl}phenyl)carbamate

生成物 1

HCID 67545272HCID 67545272、化合物収率 85%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

NaH (95%, 11 mg, 0.435 mmol) was added to a suspension of tert-butyl 4-[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]phenylcarbamate (Example 74) (120 mg, 0.217 mmol) in DMF (3 mL) at 0° C. After stirring at 0° C. for 15 min, iodomethane (0.020 mL, 0.321 mmol) was added. The reaction mixture was warmed to room temperature, stirred for additional 17 hrs, and then diluted with H2O. The resulting precipitate was collected by filtration and dried to give tert-butyl 4-[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]phenyl(methyl)carbamate (104 mg, 85%): mp (CH2Cl2/MeOH) 205-208° C.; 1H NMR (CDCl3) δ 8.42 (d, J=8.8 Hz, 2H), 8.09 (dd, J=8.4, 0.6 Hz, 1H), 7.63 (t, JHF=53.5 Hz, 1H), 7.45-7.40 (m, 3H), 6.86 (d, J=7.8 Hz, 1H), 4.13 (m, 2H), 4.07 (s, 3H), 4.00 (m, 2H), 3.86 (m, 4H), 3.35 (s, 3H), 1.50 (s, 9H); Anal. Calcd. for C28H31F2N7O4: C, 59.25; H, 5.5; N, 17.3. Found: C, 59.0; H, 5.3; N, 17.2%.

後処理

  1. temperatureThe reaction mixture was warmed to room temperature
  2. stirringstirred for additional 17 hrs
  3. filtrationThe resulting precipitate was collected by filtration
  4. customdried

出典と根拠

ORDレコード
ord-f9a26fe7a1714647b379826196c84d8c
出典データセット
uspto-grants-2013_06
特許番号
US08461158B2

反応ノート

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