Hydrochloric Acid → HCID 178440879, compound

HRID 2373775Notes

Reaction equation

HRID 2373775 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].[NH2:21][CH2:22][C:23]1[CH:24]=[C:25]([NH:29][C:30]([C:32]2[S:33][CH:34]=[CH:35][CH:36]=2)=[NH:31])[CH:26]=[CH:27][CH:28]=1.Cl.[OH:38]N1C2C=CC=CC=2N=N1.Cl.CN(C)[CH2:51][CH2:52][CH2:53]N=C=NCC.CCN(CC)CC>C(Cl)Cl.O>[C:12]([C:9]1[CH:8]=[C:7]([CH2:53][CH2:52][C:51]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][C:30](=[NH:31])[C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)[CH:24]=2)=[O:38])[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:10]=1[OH:11])([CH3:15])([CH3:14])[CH3:13]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21692686HCID 21692686, compoundHCID 178512010HCID 178512010, 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.2 HCl (J. Med. Chem. (1998), 41(15), 2858), 1.48; (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-4b8afd3b71c447488a26c678072669d1
Source dataset
uspto-grants-2008_12
Patent number
US07459558B2

Reaction notes

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