Triethylamine → 4-[4-(3-Chloro-4-trifluoromethoxy-phenyl)-7-oxo-[1,4]diazepan-1-yl]-butyric acid methyl ester

HRID 2095521Notes

Reaction equation

HRID 2095521 reaction equation
Cl.Cl.[CH3:3][O:4][C:5](=[O:30])[CH2:6][CH2:7][CH2:8][NH:9][CH2:10][CH2:11][N:12]([CH2:25][CH2:26][C:27](O)=[O:28])[C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[C:15]([Cl:24])[CH:14]=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:3][O:4][C:5](=[O:30])[CH2:6][CH2:7][CH2:8][N:9]1[C:27](=[O:28])[CH2:26][CH2:25][N:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:22])([F:21])[F:23])=[C:15]([Cl:24])[CH:14]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 866526914-{2-[(2-Carboxy-ethyl)-(3-chloro-4-trifluoromethoxy-phenyl)-amino]-ethylamino}-butyric acid methyl ester dihydrochloride

Product 1

HCID 670745194-[4-(3-Chloro-4-trifluoromethoxy-phenyl)-7-oxo-[1,4]diazepan-1-yl]-butyric acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.16 g (0.3 mmol) of 4-{2-[(2-carboxy-ethyl)-(3-chloro-4-trifluoromethoxy-phenyl)-amino]-ethylamino}-butyric acid methyl ester dihydrochloride in 2.5 ml CH2Cl2 was treated with 0.04 ml (0.3 mmol) of triethylamine and at 0° C. with 0.08 g (0.4 mmol) of EDCI. The cooling bath was allowed to come to RT and after 15 h the reaction was extracted with aqueous 10% KHSO4/Et2O (3×). The organic phases were washed with 10% KHSO4, 10% NaCl and dried over Na2SO4 to yield after evaporation of the solvent 0.11 g (76%) of the title compound as a yellow oil. MS: 409.11 (MH+, Cl).

Workup

  1. extractionthe reaction was extracted with aqueous 10% KHSO4/Et2O (3×)
  2. washThe organic phases were washed with 10% KHSO4, 10% NaCl
  3. dry with materialdried over Na2SO4
  4. customto yield
  5. customafter evaporation of the solvent 0.11 g (76%) of the title compound as a yellow oil

Sources & evidence

ORD record
ord-578f730909c8443098410bde15542dcf
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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