Triethylamine → (R)-3-(2,6-Difluoro-phenyl)-N-[2-hydroxy-1-(7-methoxy-naphthalen-2-yl)-ethyl]-acrylamide

HRID 1825055Notes

Reaction equation

HRID 1825055 reaction equation
[NH2:1][C@H:2]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[CH:10][CH:11]=2)[CH:6]=1)[CH2:3][OH:4].[F:17][C:18]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:19]=1[CH:20]=[CH:21][C:22](O)=[O:23].CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[F:17][C:18]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:19]=1[CH:20]=[CH:21][C:22]([NH:1][C@H:2]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[CH:10][CH:11]=2)[CH:6]=1)[CH2:3][OH:4])=[O:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 517784(2E)-3-(2,6-difluorophenyl)acrylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58633291(R)-2-Amino-2-(7-methoxy-naphthalen-2-yl)-ethanol

Product 1

HCID 69593452(R)-3-(2,6-Difluoro-phenyl)-N-[2-hydroxy-1-(7-methoxy-naphthalen-2-yl)-ethyl]-acrylamideYield 65.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (R)-2-Amino-2-(7-methoxy-naphthalen-2-yl)-ethanol (0.1 mmol), 2,6-difluorocinnamic acid (0.1 mmol), EDC·HCl (0.2 mmol), DMAP 0.1 mmol), triethyl amine (0.3 mmol) in dichloromethane (2 mL) was stirred at room temperature for 14 h. The reaction mixture was purified by flash chromatography eluting with 5% methnol in ethyl acetate to provide the title compound as a solid (25 mg).

Workup

  1. customThe reaction mixture was purified by flash chromatography
  2. washeluting with 5% methnol in ethyl acetate

Sources & evidence

ORD record
ord-589037255f1d46e797506be03a1fef14
Source dataset
uspto-grants-2006_05
Patent number
US07045551B2

Reaction notes

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