Triethylamine → HCID 69851383, compound

HRID 2307461Notes

Reaction equation

HRID 2307461 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.[F:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([NH2:22])[CH3:21])=[CH:16][C:15]=1[N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.CCN=C=NCCCN(C)C.Cl.CCN(CC)CC>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]([NH:22][C:8](=[O:10])[CH:7]=[CH:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:12][CH:11]=2)[CH3:21])=[CH:16][C:15]=1[N:23]1[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 980703-(4-Fluorophenyl)-2-propenoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22605564HCID 22605564, compound

Product 1

HCID 69851383HCID 69851383, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-fluorocinnamic acid (3.16 g, 19.6 mmol), 1-(4-Fluoro-3-morpholin-4-yl-phenyl)-ethylamine (4.39 g, 19.1 mmol), EDC.HCl (7.53 g, 39.2 mmol), DMAP (2.39 g, 19.6 mmol) and Et3N (8.23 ml, 58.8 mmol) in CH2Cl2 (60 ml) was stirred at room temperature for 16 hours. Purification by flesh chromatography over silica gel (elution with 50% ethyl acetate in hexane) gave 6.9 g of the title compound. The enantiomer was separated by Chiralpak AD column (50×500 mm, 20um) eluted with 45% EtOH in hexane, RT=36.1 min.

Workup

  1. customPurification by flesh chromatography over silica gel (elution with 50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-1a75fd8073d849eb876e15f9499adc46
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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