Triethylamine → HCID 67342816, compound

HRID 1669257Notes

Reaction equation

HRID 1669257 reaction equation
[CH:1]1([CH2:7][CH:8]([S:25][C:26]2[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=2)[C:9]2[CH:10]=[N:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:42][O:43][C:44](=[O:48])[CH2:45][CH2:46][NH2:47].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:42][O:43][C:44](=[O:48])[CH2:45][CH2:46][NH:47][C:30](=[O:31])[C:29]1[CH:28]=[CH:27][C:26]([S:25][CH:8]([C:9]2[CH:10]=[N:11][C:12]([C:15]3[CH:16]=[CH:17][C:18]([C:21]([F:23])([F:24])[F:22])=[CH:19][CH:20]=3)=[CH:13][CH:14]=2)[CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 192794Methyl beta-alanateHCID 67343366HCID 67343366, compound

Product 1

HCID 67342816HCID 67342816, compoundYield 31.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-{2-cyclohexyl-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethylsulfanyl}-benzoic acid (100 mg, 0.5 mmol) in methylene chloride (5 mL) are added triethyl amine (0.09 mL, 0.62 mmol), DMAP (5.0 mg), 3-amino-propionic acid methyl ester (86.2 mg, 0.62 mmol) and EDCI (118.7 mg, 0.62 mmol) at room temperature. The reaction mixture is stirred at room temperature overnight, loaded on silica gel, eluted with eluted with hexanes with a gradient from 0% of ethyl acetate to 100% of ethyl acetate giving 3-(4-{2-cyclohexyl-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethylsulfanyl}-benzoylamino)-propionic acid methyl ester (90 mg).

Workup

  1. washeluted
  2. washwith eluted with hexanes with a gradient from 0% of ethyl acetate to 100% of ethyl acetate

Sources & evidence

ORD record
ord-6b01e7ff2b914eba998e66806922a856
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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