Triethylamine → HCID 86660590, compound

HRID 718731Notes

Reaction equation

HRID 718731 reaction equation
Br[CH2:2][C:3]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7]C)=O.Cl.[NH2:17][C:18]1([CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31](=[O:40])[O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:23][CH2:22][C:21](=[O:24])[NH:20][C:19]1=[O:25].C(N(CC)CC)C>CN(C=O)C>[N+:13]([C:12]1[CH:11]=[CH:10][CH:9]=[C:4]2[C:3]=1[CH2:2][N:17]([C:18]1([CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31](=[O:40])[O:32][CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:23][CH2:22][C:21](=[O:24])[NH:20][C:19]1=[O:25])[C:5]2=[O:7])([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1487795Methyl 2-(bromomethyl)-3-nitrobenzoateHCID 86660583HCID 86660583, compound

Product 1

HCID 86660590HCID 86660590, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 18 (0.25 g, 0.912 mmol) and 4 (0.337 g, 0.912 mmol) in DMF (3.0 mL) was added triethylamine (0.320 mL, 2.28 mmol) and resulting mixture was stirred at 114° C. to 130° C. After 18 h, the mixture was cooled and concentrated. Purification by flash chromatography (95:5 DCM:MeOH) afforded 19 (0.27 g, 60%) as a light brown fluffy solid. 1H NMR (400 MHz, DMSO) δ 10.99 (s, 1H), 8.45 (d, J=8.2 Hz, 1H), 8.08 (d, J=7.6 Hz, 1H), 7.94 (s, 1H), 7.80 (dd, J=7.8 Hz, 7.8 Hz, 1H), 7.44-7.19 (m, 5H), 5.17-4.84 (m, 4H), 3.05-2.96 (m, 2H), 2.69-2.52 (m, 3H), 2.20-1.94 (m, 3H), 1.35 (m, 4H). MS (ESI) m/z calcd for C25H27N4O7 [M+H]+ 495.5, found 495.9.

Workup

  1. customresulting mixture
  2. temperaturethe mixture was cooled
  3. concentrationconcentrated
  4. customPurification by flash chromatography (95:5 DCM:MeOH)

Sources & evidence

ORD record
ord-f86bf381dceb405a838a92969867f455
Source dataset
uspto-grants-2015_11
Patent number
US09193989B2

Reaction notes

Loading…