Triethylamine → HCID 17866210, compound

HRID 1856795Notes

Reaction equation

HRID 1856795 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][C:10]([O:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])=[CH:11][CH:12]=2)[CH2:7]1.Cl.[NH2:25][C:26]1[CH:36]=[CH:35][C:29](/[CH:30]=[CH:31]/[C:32](O)=[O:33])=[CH:28][CH:27]=1.C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1>ClCCl>[NH2:25][C:26]1[CH:27]=[CH:28][C:29](/[CH:30]=[CH:31]/[C:32]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[CH2:15][CH2:14][C:13]3[C:8](=[CH:9][C:10]([O:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])=[CH:11][CH:12]=3)[CH2:7]2)=[O:33])=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 6504402139223-62-4HCID 22132518HCID 22132518, compound

Product 1

HCID 17866210HCID 17866210, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(4-aminobutyl)-7-trifluoromethylsulfonyloxy-1,2,3,4-tetrahydroisoquinoline (440 mg, 1.25 mmol), trans-4-aminocinnamic acid hydrochloride (250 mg, 1.25 mmol), triethylamine (0.174 ml, 1.25 mmol) 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (240 mg, 1.25 mmol) and 1-hydroxybenzotriazole (100 mg, 0.74 mmol) in dichloromethane (50 ml) was stirred at room temperature for 18 h. The reaction mixture was washed with saturated aqueous sodium hydrogen carbonate (50 ml) and the organic layer dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica using 10-100% ethyl acetate-hexane gradient elution to afford the title compound (280 mg, 45%).

Workup

  1. washThe reaction mixture was washed with saturated aqueous sodium hydrogen carbonate (50 ml)
  2. dry with materialthe organic layer dried (Na2SO4)
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica using 10-100% ethyl acetate-hexane gradient elution

Sources & evidence

ORD record
ord-8cb67335017743538705b056b2e75e24
Source dataset
uspto-grants-2000_11
Patent number
US06143762

Reaction notes

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