1,1'-Carbonyldiimidazole → HCID 53476929, 화합물

HRID 1505219노트

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HRID 1505219 반응식
[N:1]1([C:7]2[C:12]([CH2:13][NH2:14])=[CH:11][CH:10]=[C:9]([C:15]([F:18])([F:17])[F:16])[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1N=CN([C:24]([N:26]2C=N[CH:28]=[CH:27]2)=[O:25])C=1.NC1C2[O:38][CH2:39][C:40](=[O:42])[NH:41][C:36]=2[CH:35]=[CH:34][CH:33]=1>C1COCC1.CN(C=O)C>[O:42]=[C:40]1[NH:41][C:36]2[CH:35]=[CH:34][CH:33]=[C:27]([NH:26][C:24]([NH:14][CH2:13][C:12]3[C:7]([N:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)=[N:8][C:9]([C:15]([F:18])([F:16])[F:17])=[CH:10][CH:11]=3)=[O:25])[C:28]=2[O:38][CH2:39]1

참가 물질

6

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 115934888-Amino-2H-1,4-benzoxazin-3(4H)-oneHCID 58873540HCID 58873540, 화합물

생성물 1

HCID 53476929HCID 53476929, 화합물수율 13%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

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온도
100 °C

실험 절차

To a solution of 29f (0.48 g, 1.85 mmol) in THF (20 mL) was added CDI (2.1 mol eq, 0.63 g) and the mixture was heated for 5 h. 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. The oil obtained (0.78 g, quantitative yield) was dissolved in DMF (20 mL) and the bicyclic amine 1f was added (0.8 mol eq, 0.23 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 (1:1 EtoAc:petroleum ether) to obtain the product as a pale yellow solid (0.067 g, 13% Yield). 1HNMR (DMSO, 400 MHz) δ 1.62 (m, 6H), 3.09 (m, 4H), 4.33 (d, 2H, J=6), 4.62 (s, 2H), 6.46 (dd, 1H, J=2), 6.81 (t, 1H, J=8), 7.42 (bt, 1H), 4.46 (d, 1H, J=8), 7.74 (m, 2H), 8.20 (s, 1H), 10.66 (s, 1H). [M+1] 450.02 (C21H22F3N5O3 requires 449.43).

후처리

  1. temperature0.63 g) and the mixture was heated for 5 h
  2. customThe reaction mixture was evaporated
  3. additionwater was added
  4. extractionthe aqueous phase was extracted with EtOAc (3×20 mL)
  5. customevaporated at reduced pressure
  6. customThe oil obtained (0.78 g, quantitative yield)
  7. custom0.23 g), then the mixture obtained
  8. customThe solvent was removed at reduced pressure
  9. customthe residue was purified by chromatography (1:1 EtoAc:petroleum ether)

출처 및 근거

ORD 기록
ord-5015d08170ba4403afe082485a7d1dca
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216975B2

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