Thiopheneethanamine → HCID 59730346, compound

HRID 228299Notes

Reaction equation

HRID 228299 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([CH:18]=O)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([NH2:13])=[O:12])=[N:9][CH:10]=1.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH2:25][CH2:26][NH2:27]>>[Cl:1][C:2]1[CH:17]=[C:16]([CH2:18][NH:27][CH2:26][CH2:25][C:21]2[S:20][CH:24]=[CH:23][CH:22]=2)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([NH2:13])=[O:12])=[N:9][CH:10]=1

Participants

3

Reactant 2

HCID 116521ThiopheneethanamineHCID 59730123HCID 59730123, compound

Product 1

HCID 59730346HCID 59730346, compoundYield 72.9%

Procedure

Using a method similar to Example 405, using 5-(2-chloro-4-formylphenoxy)pyridine-2-carboxamide (0.0388 g, 0.140 mmol) and 2-(2-thienyl)ethylamine (0.018 g, 0.140 mmol) gives the title compound (0.0396 g, 72.8%): TOF MS ES+ 388.1 (M+H)+. HRMS calcd for C19H19N2O2ClS 388.0887 (M+H)+, found 388.0866, time 0.39 min; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), 0.1% TFA/acetonitrile in 0.1% TFA/water at 1.0 mL/min, 20-99% over 23 min], tR=7.6 min, 100% purity.

Sources & evidence

ORD record
ord-7e816b30401f42428f1e496f417a6117
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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