Triethylamine → HCID 57905024, compound

HRID 1093141Notes

Reaction equation

HRID 1093141 reaction equation
[CH3:1][N:2]([C:4](=[O:28])[C:5]([N:7]([CH3:27])[C:8]12[CH2:16][CH2:15][CH:12]([CH2:13][CH2:14]1)[CH2:11][N:10]1[C:17](=[O:26])[C:18]([OH:25])=[C:19]([C:21]([O:23]C)=O)[N:20]=[C:9]21)=[O:6])[CH3:3].[Br:29][C:30]1[C:35]([CH3:36])=[C:34]([F:37])[CH:33]=[C:32]([Br:38])[C:31]=1[CH2:39][NH2:40].CCN(CC)CC>CCO>[Br:29][C:30]1[C:35]([CH3:36])=[C:34]([F:37])[CH:33]=[C:32]([Br:38])[C:31]=1[CH2:39][NH:40][C:21]([C:19]1[N:20]=[C:9]2[C:8]3([N:7]([CH3:27])[C:5](=[O:6])[C:4]([N:2]([CH3:1])[CH3:3])=[O:28])[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16]3)[CH2:11][N:10]2[C:17](=[O:26])[C:18]=1[OH:25])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 57905100(2,6-Dibromo-4-fluoro-3-methylphenyl)methanamineHCID 57905168HCID 57905168, compound

Product 1

HCID 57905024HCID 57905024, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 10-(((dimethylamino)(oxo)acetyl)(methyl)amino)-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylate (0.10 g, 0.246 mmol), (2,6-dibromo-4-fluoro-3-methylphenyl)methanamine (0.225 g, 0.758 mmol) and Et3N (0.279 mL, 2 mmol) in EtOH (5 mL) was heated at reflux for 48 h. Then, cooled and purified by preparative HPLC to afford the title compound (0.0906 g, 0.138 mmol, 56% yield) as a white solid after crystallization from methanol/H2O. 1H NMR (500 MHz, CDCl3) δ: 12.18 (1 H, s), 9.08 (1 H, s), 7.32 (1 H, d, J=8.5 Hz), 4.96 (2 H, d, J=8.2 Hz), 4.78-4.90 (1 H, m), 3.57-3.72 (1 H, m), 3.36-3.49 (1 H, m), 2.94 (3 H, s), 2.93 (3 H, s), 2.76 (3 H, s), 2.48-2.54 (1 H, m), 2.34 (3 H, d, J=2.1 Hz), 2.00-2.10 (4 H, m), 1.71-1.87 (2 H, m), 1.45-1.53 (1 H, m). LCMS (M+H) calcd for C25H29Br2FN5O5: 656.05; found: 656.24.

Workup

  1. temperatureat reflux for 48 h
  2. temperatureThen, cooled
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-1daef70ad2d94c9cbcf1922246d381e8
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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