(8R)-2-Methyl-7,8-dihydro[1,4]dioxino[2,3-g][1,3]benzoxazol-8-ylmethyl 4-methylbenzenesulfonate → HCID 178432067、化合物

HRID 1072458

反応式

HRID 1072458 の反応式
[CH3:1][C:2]1[O:26][C:5]2=[C:6]3[C:11](=[CH:12][CH:13]=[C:4]2[N:3]=1)[O:10][CH2:9][C@H:8]([CH2:14]OS(C1C=CC(C)=CC=1)(=O)=O)[O:7]3.[F:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][CH:32]=[C:31]2[C@@H:37]1[CH2:42][CH2:41][C@H:40]([NH2:43])[CH2:39][CH2:38]1>CS(C)=O>[F:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][CH:32]=[C:31]2[C@@H:37]1[CH2:42][CH2:41][C@H:40]([NH:43][CH2:14][C@H:8]2[CH2:9][O:10][C:11]3[CH:12]=[CH:13][C:4]4[N:3]=[C:2]([CH3:1])[O:26][C:5]=4[C:6]=3[O:7]2)[CH2:39][CH2:38]1

参加物

4

反応物 2

HCID 11245807(8R)-2-Methyl-7,8-dihydro[1,4]dioxino[2,3-g][1,3]benzoxazol-8-ylmethyl 4-methylbenzenesulfonateHCID 178511503HCID 178511503、化合物

生成物 1

HCID 178432067HCID 178432067、化合物収率 43%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

Toluene-4-sulfonic acid (8R)-2-methyl-7,8-dihydro-1,6,9-trioxa-3-aza-cyclopenta[a]naphthlen-8-ylmethyl ester (0.52 g, 1.39 mmole) and cis-4-(5-fluoro-1H-indol-3-yl)-cyclohexylamine (0.60 g, 2.6 mmole) were combined in 10 mL of anhydrous DMSO under nitrogen. This solution was heated to 80° C. under nitrogen for 5 hours. After cooling to room temperature, the reaction was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was washed with brine, dried over magnesium sulfate and concentrated in vacuo. Flash chromatography on silica gel (CH2Cl2 then 1% MeOH/CH2Cl2) afforded 0.26 g of the title compound as a light yellow solid: m.p. 80-82° C.; MS (ESI) m/z 436 (M+H)+.

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe reaction was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-431227d2de4b477ebed10df644721b6e
出典データセット
uspto-grants-2005_06
特許番号
US06911445B2

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