1,1'-Carbonyldiimidazole → HCID 53476816, compound

HRID 1505233Notes

Reaction equation

HRID 1505233 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1N=CN([C:18](N2C=NC=C2)=[O:19])C=1.[NH2:25][C:26]1[C:31]2[O:32][CH2:33][C:34](=[O:36])[NH:35][C:30]=2[CH:29]=[CH:28][CH:27]=1>C1COCC1.CN(C=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][C:18]([NH:25][C:26]2[C:31]3[O:32][CH2:33][C:34](=[O:36])[NH:35][C:30]=3[CH:29]=[CH:28][CH:27]=2)=[O:19])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 27356554-tert-ButylbenzylamineHCID 115934888-Amino-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 53476816HCID 53476816, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-tert-butylbenzylamine (2 mL, 11.36 mmol) in THF (30 mL) was added CDI (2.1 mol eq, 3.86 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 (3×30 mL). The recombined organic phases were anhydrified over Na2SO4 and evaporated at reduced pressure (pale yellow oil, quantitative yield). The oil obtained (0.58 g, 2.28 mmol) was dissolved in DMF (20 mL) and the bicyclic amine 1f was added (0.8 mol eq, 0.30 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 white solid (0.17 g, 27% Yield). 1HNMR (DMSO, 400 MHz) δ 1.26 (s, 9H), 4.24 (d, 2H, J=6), 4.60 (s, 2H), 4.45 (dd, 1H, J=2), 6.81 (t, 1H, J=10), 7.18 (d, 2H, J=8), 7.36 (d, 2H, J=8), 7.76 (dd, 1H), 8.06 (bs, 1H), 10.64 (bs, 1H). [M+1] 353.98 (C20H23N3O3 requires 353.41).

Workup

  1. customThe reaction mixture was evaporated
  2. additionwater was added
  3. extractionthe aqueous phase was extracted with EtOAc (3×30 mL)
  4. customevaporated at reduced pressure (pale yellow oil, quantitative yield)
  5. customThe oil obtained (0.58 g, 2.28 mmol)
  6. custom0.30 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 (1:1 EtOAc:petroleum ether)

Sources & evidence

ORD record
ord-f9510294756040069c9170bc5a350790
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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