Triethylamine → HCID 69216443, compound

HRID 272756Notes

Reaction equation

HRID 272756 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:11][CH3:12])[CH:3]=1.[C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:16])[NH:14][NH2:15].CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:15][NH:14][C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:8])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 70091tert-Butyl carbazateHCID 936824-Chloro-o-anisic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 69216443HCID 69216443, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-chloro-2-methoxybenzoic acid (4.3 g, 23.1 mmol), tert-butyl carbazate (3.5 g, 26.5 mmol), EDCI.HCl (5.0 g, 26.1 mmol), and triethylamine (3.5 mL, 2.6 g, 25.3 mmol) in CH2Cl2 (50 mL) was stirred at room temperature overnight. The next day the reaction was diluted with EtOAc (200 mL), then washed with IM H3PO4, saturated NaHCO3, and brine. The organic layer was dried (Na2SO4), filtered, and concentrated under vacuum, giving the product (6.0 g, 87%). MS (DCI) m/e 301 & 303 (M+H)+, 318 & 320 (M+NH4)+; 1H NMR (300 MHz, CDCl3) δ 9.40 (br s, 1H), 8.15 (d, J=8.2 Hz, 1H), 7.08 (dd, J=8.2, 1.7 Hz, 1H), 6.98 (d, J=1.7 Hz, 1H), 6.67 (v br s, 1H), 4.00 (s, 3H), 1.50 (s, 9H).

Workup

  1. washwashed with IM H3PO4, saturated NaHCO3, and brine
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6cb700c4a4f642d295ae297f3bb11b2e
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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