(1-methyl-1H-imidazol-2-yl)methanol → HCID 178480589, 화합물

HRID 82759

반응식

HRID 82759 반응식
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][OH:8].CC([O-])(C)C.[K+].C1COCC1.[C:20]([C:24]1[S:28]/[C:27](=[N:29]\[C:30](=[O:42])[C:31]2[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:33][C:32]=2F)/[N:26]([CH2:43][C@H:44]2[CH2:48][CH2:47][CH2:46][O:45]2)[CH:25]=1)([CH3:23])([CH3:22])[CH3:21]>C1COCC1>[C:20]([C:24]1[S:28]/[C:27](=[N:29]\[C:30](=[O:42])[C:31]2[CH:36]=[C:35]([C:37]([F:39])([F:38])[F:40])[CH:34]=[CH:33][C:32]=2[O:8][CH2:7][C:3]2[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=2)/[N:26]([CH2:43][C@H:44]2[CH2:48][CH2:47][CH2:46][O:45]2)[CH:25]=1)([CH3:23])([CH3:21])[CH3:22]

참가 물질

5

반응물 3

HCID 573612(1-methyl-1H-imidazol-2-yl)methanolHCID 66863523KOtBu THFHCID 178441320HCID 178441320, 화합물

생성물 1

HCID 178480589HCID 178480589, 화합물수율 48.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of (1-methyl-1H-imidazol-2-yl)methanol (109 mg, 0.94 mmol) in THF (5 mL) was treated with a 1 M KOtBu/THF (0.95 mL, 0.944 mmol) and stirred for 15 min. A solution of Example 1A (190 mg, 0.47 mmol) was added to the reaction mixture and stirred for 6 hours. The reaction mixture was quenched with saturated NH4Cl solution, concentrated in vacuo and partitioned between EtOAc and brine, dried (MgSO4), filtered, and concentrated. The residue was purified by using an Analogix® Intelliflash280™ (SiO2, 0-60% ethyl acetate in hexanes) to afford the title compound (120 mg, 33% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.31 (s, 9 H), 1.50-1.66 (m, 1 H), 1.68-1.96 (m, 3 H), 3.55-3.84 (m, 5 H), 4.05-4.32 (m, 3 H), 5.29 (s, 2 H), 6.86 (s, 1 H), 7.20 (s, 1 H), 7.26 (s, 1 H), 7.52 (d, J=8.8 Hz, 1 H), 7.79 (dd, J=9.0, 2.2 Hz, 1 H), 8.01 (d, J=2.4 Hz, 1 H). MS (DCI/NH3) m/z 523 (M+H)+. Anal. calcd for C25H29F3N4O3S: C, 57.46; H, 5.59; N, 10.72. Found: C, 56.96; H, 5.57; N, 10.46.

후처리

  1. stirringstirred for 6 hours
  2. customThe reaction mixture was quenched with saturated NH4Cl solution
  3. concentrationconcentrated in vacuo
  4. custompartitioned between EtOAc and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified

출처 및 근거

ORD 기록
ord-ce5a40eec2ad49d188b91777bcbdb2af
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846730B2

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