Pyridine → HCID 68500584, compound

HRID 2387245Notes

Reaction equation

HRID 2387245 reaction equation
[O:1]=[C:2]1[NH:8][CH2:7][CH2:6][CH2:5][N:4]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:3]1.[CH:19]1(B(O)O)[CH2:21][CH2:20]1.CCN(CC)CC.N1C=CC=CC=1>C1COCC1.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH:19]1([N:8]2[CH2:7][CH2:6][CH2:5][N:4]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:10])[CH2:3][C:2]2=[O:1])[CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 2760897Cyclopropylboronic acidHCID 14437517HCID 14437517, compound

Product 1

HCID 68500584HCID 68500584, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of benzyl 3-oxo-1,4-diazepane-1-carboxylate (prepared according to Polish J. Chem. 1989, 63, 265-71), cyclopropylboronic acid (6 eq.), Et3N (10 eq.), pyridine (16 eq.) and Cu(OAc)2 (4 eq.) in dry THF (0.24 M) was heated for 10 min. to 140° C. in a microwave oven. After cooling to RT the mixture was filtered through celite, the solvents were removed under reduced pressure and the product was purified by chromatography on silica gel, eluenting with EtOAc/petroleum ether. The product was obtained as a white solid. 1H-NMR (300 MHz, CDCl3) δ: 7.45-7.22 (5H, m), 5.15 (2H, s), 4.22-4.07 (2H, m), 3.70-3.37 (4H, m), 2.75-2.60 (1H, m), 1.90-1.65 (2H, m), 0.85-0.72 (2H, m), 0.60-0.41 (2H, m). MS (ES) C16H20N2O3 requires: 288, found: 289 (M+H)+.

Workup

  1. temperaturewas heated for 10 min. to 140° C. in a microwave oven
  2. filtrationwas filtered through celite
  3. customthe solvents were removed under reduced pressure
  4. customthe product was purified by chromatography on silica gel
  5. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-9080e9ee360d433693a3a1763bb3397e
Source dataset
uspto-grants-2012_09
Patent number
US08268827B2

Reaction notes

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