Acetic Acid → HCID 89925772、化合物

HRID 2280210ノート

反応式

HRID 2280210 の反応式
[NH2:1][C:2]1[S:14][C:13]2[CH2:12][C@@H:11]3[C@H:6]([CH2:7][C@@H:8]([C:16]([N:18]([CH2:27][CH2:28][CH3:29])[C:19]([NH:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])=[O:20])=[O:17])[CH2:9][N:10]3[CH3:15])[CH2:5][C:4]=2[C:3]=1[C:30]#[N:31].[C:32](O)(=[O:34])[CH3:33]>>[C:30]([C:3]1[C:4]2[CH2:5][C@@H:6]3[C@@H:11]([CH2:12][C:13]=2[S:14][C:2]=1[NH:1][C:32](=[O:34])[CH3:33])[N:10]([CH3:15])[CH2:9][C@H:8]([C:16]([N:18]([C:19](=[O:20])[NH:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[CH2:27][CH2:28][CH3:29])=[O:17])[CH2:7]3)#[N:31]

参加物

3

反応物 2

HCID 176Acetic AcidHCID 66548529Matsupexole

生成物 1

HCID 89925772HCID 89925772、化合物

反応条件

温度
135 °C

実験手順

To 1-{[(4aR*,6R*,8aR*)-2-amino-3-cyano-8-methyl-4H,4aH,5H,6H,7H,8H, 8aH,9H-thieno[3,2-g]quinolin-6-yl]carbonyl}-3-[2-(dimethylamino)ethyl]-1-propylurea (example 1-15) (100 mg) was added acetic acid (2 mL) and the mixture was heated at 135° C. and refluxed for 12 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. To the residue were added ethyl acetate and a saturated aqueous solution of sodium bicarbonate. After the separated organic layer was dried over anhydrous sodium sulfate, it was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 0%-5% methanol/ethyl acetate, gradient elution) to give the title compound (26 mg). The structure was illustrated in Table 11.

後処理

  1. temperaturerefluxed for 12 hours
  2. temperatureAfter cooling to room temperature
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. additionTo the residue were added ethyl acetate
  5. dry with materialAfter the separated organic layer was dried over anhydrous sodium sulfate, it
  6. concentrationwas concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: 0%-5% methanol/ethyl acetate, gradient elution)

出典と根拠

ORDレコード
ord-f15f7a27c26e4f7589d1f815c9e2a061
出典データセット
uspto-grants-2015_09
特許番号
US09138434B2

反応ノート

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