Triethylamine → HCID 178440879, compound

HRID 1988362Notes

Reaction equation

HRID 1988362 reaction equation
[C:1]([C:5]1[CH:6]=[C:7](C(C)C(O)=O)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[NH2:23][CH2:24][C:25]1[CH:26]=[C:27]([NH:31][C:32]([C:34]2[S:35][CH:36]=[CH:37][CH:38]=2)=[NH:33])[CH:28]=[CH:29][CH:30]=1.[OH:39]N1C2C=CC=CC=2N=N1.Cl.CN(C)[CH2:52][CH2:53][CH2:54]N=C=NCC.CCN(CC)CC>C(Cl)Cl.O>[C:12]([C:9]1[CH:8]=[C:7]([CH2:54][CH2:53][C:52]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][C:32](=[NH:33])[C:34]3[S:35][CH:36]=[CH:37][CH:38]=3)[CH:26]=2)=[O:39])[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:10]=1[OH:11])([CH3:15])([CH3:14])[CH3:13]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21692686HCID 21692686, compoundHCID 178478771HCID 178478771, compound

Product 1

HCID 178440879HCID 178440879, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2.78 g (10 mmol) of 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid, 3.04 g (10 mmol) of N-[3-(aminomethyl)phenyl]thiophene-2-carboximidamide 2HCl (J. Med. Chem. (1998), 41(15), 2858), 1.48 g (11 mmol) of 1-hydroxybenzotriazole in 100 ml of CH2Cl2, in a 250 ml flask, 4.21 g (22 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 6.1 ml (44 mmol) of Et3N were added. After overnight stirring at 20° C., the reaction mixture was diluted with 100 ml water, stirred and decanted. The organic layer was successively washed with NaHCO3 saturated solution, water, KHSO4, (1M), water and brine. After drying over Na2SO4 and filtration, the organic solution was concentrated under reduced pressure. The residue was flash chromatographed over silica gel, using heptane/EtOAc:1/1 as eluent, to yield a cream light solid (85%). Melting point: 163-164° C.

Workup

  1. stirringstirred
  2. customdecanted
  3. washThe organic layer was successively washed with NaHCO3 saturated solution, water, KHSO4, (1M), water and brine
  4. dry with materialAfter drying over Na2SO4 and filtration
  5. concentrationthe organic solution was concentrated under reduced pressure
  6. customchromatographed over silica gel

Sources & evidence

ORD record
ord-ddf76202f0374363987b8f3393f19969
Source dataset
uspto-grants-2009_06
Patent number
US07553976B2

Reaction notes

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