1,1'-Carbonyldiimidazole → HCID 53476358、化合物

HRID 1505188ノート

反応式

HRID 1505188 の反応式
[NH2:1][CH2:2][C:3]1[O:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1.C1N=CN([C:17]([N:19]2C=N[CH:21]=[CH:20]2)=[O:18])C=1.NC1C2[O:32][C:31](=[O:34])[NH:30][C:29]=2[CH:28]=[CH:27][CH:26]=1>C1COCC1.CN(C=O)C>[O:32]=[C:31]1[NH:30][C:29]2[CH:28]=[CH:27][CH:26]=[C:20]([NH:19][C:17]([NH:1][CH2:2][C:3]3[O:4][C:5]([C:8]([F:11])([F:9])[F:10])=[CH:6][CH:7]=3)=[O:18])[C:21]=2[O:34]1

参加物

6

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 111478147-Amino-2(3H)-benzoxazoloneHCID 185259182-(Aminomethyl)-5-(trifluoromethyl)furan

生成物 1

HCID 53476358HCID 53476358、化合物収率 13%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

To a solution of 2-aminomethyl-5-trifluoromethylfurane (1 g, 6.1 mmol) in THF (30 mL) was added CDI (2.1 mol eq) and the mixture was heated at 70° C. overnight. The reaction mixture was evaporated, water was added and the aqueous phase was extracted with EtOAc (3×20 mL). The recombined organic phases were anhydrified over Na2SO4 and evaporated at reduced pressure (1.6 g, 5.9 mmol). The oil obtained (0.31 g, 1.19 mmol) was dissolved in DMF (20 mL) and the bicyclic amine 1c (Scheme 3) was added (0.8 mol eq, 0.15 g), then the mixture obtained was heated at 100° C. overnight. The solvent was removed at reduced pressure and the residue was purified by chromatography (100% EtOAc) to obtain the product as white solid (0.05 g, 13% Yield). 1HNMR (DMSO, 200 MHz) δ 4.37 (d, 2H, J=6), 6.48 (d, 1H, J=2), 6.70 (dd, 1H), 7.01 (m, 2H), 7.16 (m, 1H), 7.70 (dd, 1H, J=2), 8.69 (s, 1H), 11.62 (bs, 1H). [M+1] 341.61 (C14H10F3N3O4 requires 341.24).

後処理

  1. customThe reaction mixture was evaporated
  2. additionwater was added
  3. extractionthe aqueous phase was extracted with EtOAc (3×20 mL)
  4. customevaporated at reduced pressure (1.6 g, 5.9 mmol)
  5. customThe oil obtained (0.31 g, 1.19 mmol)
  6. custom0.15 g), then the mixture obtained
  7. temperaturewas heated at 100° C. overnight
  8. customThe solvent was removed at reduced pressure
  9. customthe residue was purified by chromatography (100% EtOAc)

出典と根拠

ORDレコード
ord-b320ce65f4e54ef998817210b5391edf
出典データセット
uspto-grants-2015_12
特許番号
US09216975B2

反応ノート

読み込み中…