Methyl iodide → HCID 86670144, 화합물

HRID 2169602노트

반응식

HRID 2169602 반응식
[H-].[Na+].[Cl:3][C:4]1[N:13]=[CH:12][C:11]2[N:10]([CH2:14][C:15]([NH:17][CH2:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[O:16])[CH2:9][C@@H:8]3[CH2:25][O:26][CH2:27][CH2:28][N:7]3[C:6]=2[N:5]=1.CI.[CH3:31]COC(C)=O>CN(C=O)C>[Cl:3][C:4]1[N:13]=[CH:12][C:11]2[N:10]([CH2:14][C:15]([N:17]([CH3:31])[CH2:18][CH:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)=[O:16])[CH2:9][C@@H:8]3[CH2:25][O:26][CH2:27][CH2:28][N:7]3[C:6]=2[N:5]=1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 86670145HCID 86670145, 화합물

생성물 1

HCID 86670144HCID 86670144, 화합물수율 70.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Sodium hydride (60% in oil) (12.57 mg, 0.314 mmol) was added to a suspension of (R)-2-(2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide (PREPARATION x26, 100 mg, 0.262 mmol) in DMF (1 mL) at 0° C. The resultant mixture was stirred at room temperature for 30 minutes. Methyl iodide (0.021 mL, 0.340 mmol) was added to the reaction mixture at room temperature, and the resultant mixture was stirred at room temperature for 15 minutes. After addition of EtOAc, the resultant mixture was washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was washed with EtOAc to afford the title compound as a white solid (73 mg, 70.4%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.04-1.38 (m, 2 H), 1.48 (d, J=11.12 Hz, 2 H), 1.75-1.99 (m, 1 H), 2.80-3.01 (m, 4 H), 3.09-3.31 (m, 7 H), 3.40-3.64 (m, 2 H), 3.79-4.06 (m, 5 H), 4.17-4.27 (m, 1 H), 4.34-4.44 (m, 1 H), 7.12-7.29 (m, 1 H); ESI-MS m/z [M+H]+ calc'd for C18H26ClN5O3, 396.18; found 396.3.

후처리

  1. washthe resultant mixture was washed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washThe residue was washed with EtOAc

출처 및 근거

ORD 기록
ord-d6ae0fa1cfde488db0d0888fc901d5f6
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045496B2

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