Triethylamine → HCID 57904734, compound

HRID 1093149Notes

Reaction equation

HRID 1093149 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:31][CH:15]([CH2:16][CH2:17][N:18]3[C:23](=[O:24])[C:22]([OH:25])=[C:21]([C:26](OCC)=[O:27])[N:20]=[C:19]31)[O:14][CH2:13]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][NH2:40])=[CH:35][CH:34]=1.CCN(CC)CC>CCO>[F:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][NH:40][C:26]([C:21]2[N:20]=[C:19]3[N:18]([C:23](=[O:24])[C:22]=2[OH:25])[CH2:17][CH2:16][CH:15]2[CH2:31][C:12]3([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:13][O:14]2)=[O:27])=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 57905029HCID 57905029, compound

Product 1

HCID 57904734HCID 57904734, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 11-(((benzyloxy)carbonyl)amino)-3-hydroxy-4-oxo-7,8,10,11-tetrahydro-4 H,6H-8,11-methanopyrimido[2,1-d][1,5]oxazocine-2-carboxylate (0.070 g, 0.163 mmol), (4-fluorophenyl)methanamine (0.125 g, 1 mmol) and Et3N (0.418 mL, 3 mmol) in EtOH (5 mL) was heated at reflux for 7 h. The reaction was cooled, concentrated and the residue purified by preparative-HPLC to afford title compound (0.0405 g, 0.080 mmol, 49%) as an off-white solid. 1H NMR (500 MHz, CDCl3) δ: 11.99 (0.6 H, brs), 11.92 (0.4 H, brs), 7.82 (0.4 H, t, J=5.8 Hz), 7.58 (0.6 H, t, J=5.8 Hz), 7.32-7.39 (3 H, m), 7.17-7.28 (2 H, m), 7.09 (1 H, dd, J=8.1, 5.6 Hz), 7.01-7.06 (1 H, m), 6.91-6.99 (2 H, m), 5.60 (0.6 H, s), 5.41-5.51 (1 H, m), 5.10 (0.4 H, s), 5.02 (0.6 H, d, J=12.5 Hz), 4.89 (1 H, d, JAB=12.4 Hz.), 4.79 (0.6 H, d, J=10.7 Hz), 4.69-4.75 (2 H, m), 4.60 (0.4 H, d, J=10.4 Hz), 4.37-4.49 (2.8 H, m), 4.12 (0.6 H, dd, J=18.8, 6.0 Hz), 3.70 (0.6 H, t, J=13.7 Hz), 3.63 (0.4 H, t, J=13.7 Hz), 2.47-2.60 (1 H, m), 2.13-2.21 (1 H, m.), 1.97-2.05 (1 H, m). LCMS (M+H) calcd for C26H26FN4O6: 509.18; found: 509.14.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 7 h
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated
  5. customthe residue purified by preparative-HPLC

Sources & evidence

ORD record
ord-fb69b4502008477aad6aacc334481f55
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

Loading…