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Dichloromethane → (S)-N-(6,7-dihydro-2-nitro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)-3-(4-(4-(trifluoromethoxy)phenoxy)piperidin-1-yl) propanamide

HRID 1043551
ノート
印刷プレビュー

反応式

HRID 1043551 の反応式
[N+:1]([C:4]1[N:5]=[C:6]2[N:11]([CH:12]=1)[CH2:10][CH:9]([NH2:13])[CH2:8][O:7]2)([O-:3])=[O:2].CCN(CC)CC.[F:21][C:22]([F:43])([F:42])[O:23][C:24]1[CH:41]=[CH:40][C:27]([O:28][CH:29]2[CH2:34][CH2:33][N:32]([CH2:35][CH2:36][C:37](Cl)=[O:38])[CH2:31][CH2:30]2)=[CH:26][CH:25]=1.ClCCl>CN(C=O)C>[N+:1]([C:4]1[N:5]=[C:6]2[N:11]([CH:12]=1)[CH2:10][C@H:9]([NH:13][C:37](=[O:38])[CH2:36][CH2:35][N:32]1[CH2:31][CH2:30][CH:29]([O:28][C:27]3[CH:40]=[CH:41][C:24]([O:23][C:22]([F:21])([F:42])[F:43])=[CH:25][CH:26]=3)[CH2:34][CH2:33]1)[CH2:8][O:7]2)([O-:3])=[O:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 598406212-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-amineHCID 866859183-(4-(4-(Trifluoromethoxy)phenoxy)piperidin-1-yl) propionyl chloride

生成物 1

HCID 68206983(S)-N-(6,7-dihydro-2-nitro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)-3-(4-(4-(trifluoromethoxy)phenoxy)piperidin-1-yl) propanamide収率 23%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Under Ar, (S)-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine-6-amine (110 mg, 0.6 mmol) was dissolved in DMF (6 mL), cooled to 0° C., added Et3N (0.21 mL, 2 mmol), added 3-(4-(4-(trifluoromethoxy)phenoxy)piperidin-1-yl) propionyl chloride (291 mg, 0.75 mmol) in batches, naturally rose to room temperature and stirred for 3 h, added an appropriate amount of dichloromethane, washed by distilled water for 3 times, followed by anhydrous sodium sulphate drying, filtrated out drying agent and spinning dry, residuals were purified by column chromatography (eluent CH2Cl2: MeOH=30:1) to give 70 mg target product, yield was 23%.

後処理

  1. customnaturally rose to room temperature
  2. washwashed
  3. distillationby distilled water for 3 times
  4. filtrationfiltrated
  5. customout drying agent
  6. customspinning dry
  7. customresiduals were purified by column chromatography (eluent CH2Cl2: MeOH=30:1)
  8. customto give 70 mg target product, yield was 23%

出典と根拠

ORDレコード
ord-db94a6116aa94ef8936f50884489cfb4
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08563547B2

反応ノート

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