Chlorodifluoromethane → HCID 86664227、化合物

HRID 1184519ノート

反応式

HRID 1184519 の反応式
Cl[CH:2]([F:4])[F:3].[OH:5][C:6]1[C:11]2[O:12][CH:13]([CH3:17])[C:14](=[O:16])[NH:15][C:10]=2[CH:9]=[C:8]([CH:18]=[O:19])[CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:3][CH:2]([F:4])[O:5][C:6]1[C:11]2[O:12][CH:13]([CH3:17])[C:14](=[O:16])[NH:15][C:10]=2[CH:9]=[C:8]([CH:18]=[O:19])[CH:7]=1

参加物

5

反応物 3

HCID 6372ChlorodifluoromethaneHCID 10796Cesium carbonateHCID 866642258-Hydroxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde

生成物 1

HCID 86664227HCID 86664227、化合物収率 65.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
23 °C

実験手順

A 40 mL vial cooled in a dry ice/acetone bath was charged with chlorodifluoromethane (0.209 g, 2.413 mmol) followed by the addition of 8-hydroxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde 398A (0.5 g, 2.413 mmol), Cs2CO3 (0.786 g, 2.413 mmol) and DMF (4.83 mL). The dry ice/acetone bath was removed; and with continued stirring, the reaction was slowly warmed to 23° C. After 2.5 hr, the reaction was transferred to a sand bath and stirred at 70° C. for 72 hr. The crude material was purified by prep HPLC-MS (30-55% MeCN in water, basic mode). The fractions were collected and concentrated in vacuo to give the title compound as a white solid (0.404 g, 57% yield): 1H NMR (400 MHz, DMSO-d6) δ ppm 1.44-1.51 (m, 3H) 4.93 (q, J=6.82 Hz, 1H) 7.08-7.28 (m, 1H) 7.32 (d, J=1.77 Hz, 1H) 7.46 (d, J=1.01 Hz, 1H) 9.83-9.88 (m, 1H) 11.14 (s, 1H). ESI-MS: m/z 258.1 (M+H)+.

後処理

  1. temperatureA 40 mL vial cooled in a dry ice/acetone bath
  2. customThe dry ice/acetone bath was removed
  3. customthe reaction was transferred to a sand bath
  4. customThe crude material was purified by prep HPLC-MS (30-55% MeCN in water, basic mode)
  5. customThe fractions were collected
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-3bc579a56a05430ea3f0583ee811a026
出典データセット
uspto-grants-2014_03
特許番号
US08669249B2

反応ノート

読み込み中…