1,1'-Carbonyldiimidazole → HCID 53476358, 화합물

HRID 1505188노트

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HRID 1505188 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 53476358HCID 53476358, 화합물수율 13%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

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온도
70 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b320ce65f4e54ef998817210b5391edf
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216975B2

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