Triethylamine → HCID 21093909, compound

HRID 1767576Notes

Reaction equation

HRID 1767576 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH2:40][CH2:41][NH2:42].C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[Br:11][C:8]1[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([CH:7]=1)[C:4]([NH:42][CH2:41][CH2:40][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[Cl:33])=[O:6]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 331275-Bromo-2-chlorobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 831172-(2-Chlorophenyl)ethylamine

Product 1

HCID 21093909HCID 21093909, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-chloro-5-bromobenzoic acid (1.5 g, 6.3 mmol), EDCI (1.63 g, 8.5 mmol), and HOBT (1.15 g, 8.5 mmol) in DMF (20 ml) was added 2-(2-chlorophenyl)ethylamine (1.06 ml, 7.5 mmol). After 15 minutes triethylamine (1.18 ml, 8.5 mmol) and DMF (5 ml) was added. After 2 hours at ambient temperature the mixture was diluted with ethyl acetate (50 ml) and washed with 1 N HCl followed by a saturated solution of sodium bicarbonate, followed by water, and then brine. The organic layer was separated and dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 2.12 g of an amorphous solid. Mass Spectrum (ES+) 374.6, (ES−) 372.2.

Workup

  1. washwashed with 1 N HCl
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f81105fac6f84e0a932e719fe7b6e19c
Source dataset
uspto-grants-2007_06
Patent number
US07235549B2

Reaction notes

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