(1-methyl-1H-imidazol-2-yl)methanol → HCID 178480589、化合物

HRID 82759

反応式

HRID 82759 の反応式
[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]

参加物

5

反応物 3

HCID 573612(1-methyl-1H-imidazol-2-yl)methanolHCID 66863523KOtBu THFHCID 178441320HCID 178441320、化合物

生成物 1

HCID 178480589HCID 178480589、化合物収率 48.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ce5a40eec2ad49d188b91777bcbdb2af
出典データセット
uspto-grants-2014_09
特許番号
US08846730B2

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