2-(5-(3,4-Dichlorophenyl)furan-2-yl)ethanamine → HCID 178441079, compound

HRID 872450Notes

Reaction equation

HRID 872450 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:10]([OH:12])=O)[NH:8][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:13][C:14]1[CH:15]=[C:16]([C:21]2[O:25][C:24]([CH2:26][CH2:27][NH2:28])=[CH:23][CH:22]=2)[CH:17]=[CH:18][C:19]=1[Cl:20]>>[Cl:13][C:14]1[CH:15]=[C:16]([C:21]2[O:25][C:24]([CH2:26][CH2:27][NH:28][C:10]([C:7]3[NH:8][N:9]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:6]=3)=[O:12])=[CH:23][CH:22]=2)[CH:17]=[CH:18][C:19]=1[Cl:20]

Participants

3

Reactant 2

HCID 547757822-(5-(3,4-Dichlorophenyl)furan-2-yl)ethanamineHCID 178441096HCID 178441096, compound

Product 1

HCID 178441079HCID 178441079, compoundYield 33%

Procedure

The title compound was synthesized as in Example 17 starting from 5-tert-butyl-2H-pyrazole-3-carboxylic acid and 2-(5-(3,4-dichlorophenyl)furan-2-yl)ethanamine. Crude product was purified by chromatography (silica column, eluent: 3% MeOH/DCM) to give 53 mg (33%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 1.27 (s, 9H), 2.97 (t, 2H), 3.54 (q, 2H), 6.33 (m, 1H), 6.39 (br s, 1H), 7.02 (d, 1H), 7.62 (m, 2H), 7.86 (d, 1H), 8.20 (s, 1H), 12.88 (s, 1H).

Workup

  1. customCrude product was purified by chromatography (silica column, eluent: 3% MeOH/DCM)

Sources & evidence

ORD record
ord-b680fd4f92384774943bc7166f3b6bd8
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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