1,1'-Carbonyldiimidazole → HCID 53476929, compound

HRID 1505219Notes

Reaction equation

HRID 1505219 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 53476929HCID 53476929, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-5015d08170ba4403afe082485a7d1dca
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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