Triethylamine → (R)-3-(2-Chloro-phenyl)-N-[1-(4-fluoro-3-morpholin-4-yl-phenyl)-2-hydroxy-ethyl]-acrylamide

HRID 1825053Notes

Reaction equation

HRID 1825053 reaction equation
[NH2:1][C@H:2]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:6]=1)[CH2:3][OH:4].[Cl:18][C:19]1[CH:29]=[CH:28][CH:27]=[CH:26][C:20]=1[CH:21]=[CH:22][C:23](O)=[O:24].CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[Cl:18][C:19]1[CH:29]=[CH:28][CH:27]=[CH:26][C:20]=1[CH:21]=[CH:22][C:23]([NH:1][C@H:2]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:6]=1)[CH2:3][OH:4])=[O:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 195673-(2-Chlorophenyl)acrylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57419699(R)-2-Amino-2-(4-fluoro-3-morpholin-4-yl-phenyl)-ethanol

Product 1

HCID 69593433(R)-3-(2-Chloro-phenyl)-N-[1-(4-fluoro-3-morpholin-4-yl-phenyl)-2-hydroxy-ethyl]-acrylamideYield 71.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (R)-2-amino-2-(4-fluoro-3-morpholin-4-yl-phenyl)-ethanol (0.1 mmol), 2-chloro-cinnamic 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 with 5% methnol in ethyl acetate to provide the title compound as a solid (29 mg).

Workup

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

Sources & evidence

ORD record
ord-00a75db94c15453f906bbea73fc12d28
Source dataset
uspto-grants-2006_05
Patent number
US07045551B2

Reaction notes

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