Triethylamine → HCID 67550666, compound

HRID 2307464Notes

Reaction equation

HRID 2307464 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=O)=[CH:4][CH:3]=1.[CH3:13][O:14][C:15]([N:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][C:21]([CH:27]([NH2:29])[CH3:28])=[CH:22][CH:23]=2)[CH2:18]1)=[O:16].CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:13][O:14][C:15]([N:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][C:21]([CH:27]([NH:29][C:8](=[O:10])[CH:7]=[CH:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:12][CH:11]=3)[CH3:28])=[CH:22][CH:23]=2)[CH2:18]1)=[O:16]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 980703-(4-Fluorophenyl)-2-propenoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 20744332HCID 20744332, compound

Product 1

HCID 67550666HCID 67550666, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-fluorocinnamic acid (1 mmol), (±)-7-(1-aminoethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid methyl ester, Preparation 10 (280 mg, 1.2 mmol), EDC hydrochloride (387 mg, 2 mmol), DMAP (122 mg, 1 mmol), and triethylamine (404 mg, 4 mmol) in CH2Cl2 (8 mL) was stirred at room temperature for 16 hours. The reaction mixture was directly subjected to purification by flash column chromatography on silica gel eluted with EtOAc/hexane (50%) to provide the title compound (295 mg).

Workup

  1. customThe reaction mixture was directly subjected to purification by flash column chromatography on silica gel
  2. washeluted with EtOAc/hexane (50%)

Sources & evidence

ORD record
ord-769c35533749475fa95f2da676679d2d
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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