Triethylamine → HCID 86615990, compound

HRID 1914338Notes

Reaction equation

HRID 1914338 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH:9]([C:15]2[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=2)[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][C:3]=1[CH3:24].C(N(CC)CC)C.Cl.[CH3:33][O:34][C:35](=[O:39])[CH2:36][CH2:37][NH2:38].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:33][O:34][C:35](=[O:39])[CH2:36][CH2:37][NH:38][C:19](=[O:20])[C:18]1[CH:22]=[CH:23][C:15]([CH:9]([O:8][C:5]2[CH:6]=[N:7][C:2]([Cl:1])=[C:3]([CH3:24])[CH:4]=2)[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 86615989HCID 86615989, compound

Product 1

HCID 86615990HCID 86615990, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-[1-(6-chloro-5-methyl-pyridin-3-yloxy)-3,3-dimethyl-butyl]-benzoic acid (414 mg, 1.19 mmol) in methylene chloride (12 mL) is added triethyl amine (0.5 mL, 3.6 mmol), DMAP (5.0 mg), 3-Amino-propionic acid methyl ester hydrochloride (250 mg, 1.8 mmol) and EDCI (688 mg, 3.6 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 the titled compound (400 mg).

Workup

  1. washeluted
  2. washwith eluted with hexanes with a gradient from 0% of ethyl acetate to 100% of ethyl acetate giving the titled compound (400 mg)

Sources & evidence

ORD record
ord-79aa5a0b7a464e8f93aee6efdbbd2e0e
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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