Triethylamine → HCID 42602999, compound

HRID 1260596Notes

Reaction equation

HRID 1260596 reaction equation
[CH:1]1[CH:2]=CC2N(O)N=[N:7][C:5]=2[CH:6]=1.[CH3:11][CH2:12][N:13]=[C:14]=[N:15][CH2:16][CH2:17][CH2:18]N(C)C.[CH2:22](N(CC)CC)C.[F:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32]([OH:34])=O>CN(C=O)C>[F:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32]([N:7]1[CH2:2][CH2:1][CH:6]([C:17]2[C:18]3[C:14](=[N:13][CH:12]=[CH:11][CH:22]=3)[NH:15][CH:16]=2)[CH2:5]1)=[O:34]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 99352-Fluorobenzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-Hydroxybenzotriazole

Product 1

HCID 42602999HCID 42602999, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Previous amine (0.2 g 1.08 mmol) was dissolved in DMF (3 ml) and cooled to 0° C. Then HOBT (0.0432 g 0.318 mmol), EDCI (0.303 g 1.59 mmol) were added followed by triethylamine (0.44 ml) and 2-fluorobenzoic acid (0.178 g 1.27 mmol). The mixture was stirred at RT overnight, quenched with quenched with 20 ml of 10% sodium bicarbonate solution and extracted with ethyl acetate. Ethyl acetate was concentrated and pure product obtained by column chromatography as off white solid (0.050 g).

Workup

  1. customquenched
  2. customwith quenched with 20 ml of 10% sodium bicarbonate solution
  3. extractionextracted with ethyl acetate
  4. concentrationEthyl acetate was concentrated

Sources & evidence

ORD record
ord-259f6382d97c4a1fb89f7ab26aa8f646
Source dataset
uspto-grants-2013_06
Patent number
US08470849B2

Reaction notes

Loading…