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1,1'-Carbonyldiimidazole → 1-(3-oxo-4H-1,4-benzoxazin-8-yl)-3-[[5-(trifluoromethyl)-2-furyl]methyl]urea

HRID 1505217
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HRID 1505217 반응식
[F:1][C:2]([F:11])([F:10])[C:3]1[O:7][C:6]([CH2:8][NH2:9])=[CH:5][CH:4]=1.C1N=CN([C:17]([N:19]2C=N[CH:21]=[CH:20]2)=[O:18])C=1.NC1C2[O:31][CH2:32][C:33](=[O:35])[NH:34][C:29]=2[CH:28]=[CH:27][CH:26]=1>C1COCC1.CN(C=O)C>[O:35]=[C:33]1[NH:34][C:29]2[CH:28]=[CH:27][CH:26]=[C:20]([NH:19][C:17]([NH:9][CH2:8][C:6]3[O:7][C:3]([C:2]([F:10])([F:1])[F:11])=[CH:4][CH:5]=3)=[O:18])[C:21]=2[O:31][CH2:32]1
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참가 물질

6

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 115934888-Amino-2H-1,4-benzoxazin-3(4H)-oneHCID 185259182-(Aminomethyl)-5-(trifluoromethyl)furan

생성물 1

HCID 534765881-(3-oxo-4H-1,4-benzoxazin-8-yl)-3-[[5-(trifluoromethyl)-2-furyl]methyl]urea수율 10%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 8028
Tetrahydrofuran
용매

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온도
70 °C

실험 절차

To a solution of [5-(trifluoromethyl)-2-furyl]methanamine (0.48 g, 2.91 mmol) in THF (20 mL) was added CDI (2.1 mol eq, 0.99 g) 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 (3×25 mL). The recombined organic phases were anhydrified over Na2SO4 and evaporated at reduced pressure (yellow oil, 1.68 g, quantitative yield). The oil obtained was dissolved in DMF (20 mL) and the bicyclic amine 1f was added (0.8 mol eq, 0.57 g), then the mixture obtained was heated at 100° C. overnight. The solvent was removed at reduced pressure and the residue was purified by crystallization from a mixture of MeOH/EtOAc to afford the product as a pale yellow solid (0.088 g, 10% Yield). 1HNMR (DMSO, 400 MHz) δ 4.37 (d, 2H, J=6), 4.60 (s, 2H), 6.46 (m, 2H), 6.77 (t, 1H, J=8), 7.16 (m, 1H), 7.37 (t, 1H), 7.72 (dd, 1H, J=2), 8.16 (s, 1H), 10.64 (bs, 1H).

후처리

  1. customThe reaction mixture was evaporated
  2. additionwater was added
  3. extractionthe aqueous phase was extracted with EtOAc (3×25 mL)
  4. customevaporated at reduced pressure (yellow oil, 1.68 g, quantitative yield)
  5. customThe oil obtained
  6. custom0.57 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 crystallization from a mixture of MeOH/EtOAc

출처 및 근거

ORD 기록
ord-7d402e8ca92b476b9c893f42ea3a421d
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09216975B2

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