1,2-Dichloroethane → HCID 57948492, compound

HRID 2383529Notes

Reaction equation

HRID 2383529 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=O)=[CH:8][CH:7]=2)=[CH:2]1.Cl.[F:17][C:18]([F:30])([F:29])[CH:19]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][N:22]=1)[NH2:20].C(N(CC)CC)C.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[CH:8][C:9]([CH2:12][C:13]([NH:20][C@@H:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][N:22]=3)[C:18]([F:29])([F:17])[F:30])=[O:15])=[CH:10][CH:11]=2)=[CH:2]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 13773530HCID 13773530, compoundHCID 66893345HCID 66893345, compound

Product 1

HCID 57948492HCID 57948492, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.04 g (0.18 mmol) [4-(3-thienyl)phenyl]acetic acid in 0.75 mL DMF was added 0.06 g (0.2 mmol) 2,2,2-trifluoro-1-(5-methoxypyridin-2-yl)ethanamine hydrochloride, 0.1 mL (0.6 mmol) triethylamine, 0.03 g (0.2 mmol) HOAt, and 0.05 g (0.2 mmol) EDC and the mixture stirred for 1 hour at room temperature. Purification (no workup) by preparative reverse phase HPLC (linear gradient 5 to 95% CH3CN/H2O over 30 min, 0.05% added TFA, C18 SunFire 19×150 mm) afforded 2-[4-(3-thienyl)phenyl]-N-[(1S)-2,2,2-trifluoro-1-(5-methoxypyridin-2-yl)ethyl]acetamide high resolution mass spec calc for C20H17F3N2O2S 407.1036, found 407.1043.

Workup

  1. customPurification (no workup)
  2. additionby preparative reverse phase HPLC (linear gradient 5 to 95% CH3CN/H2O over 30 min, 0.05% added TFA, C18 SunFire 19×150 mm)

Sources & evidence

ORD record
ord-93aa3ec23e9542fcb40bd3c9c743cbc3
Source dataset
uspto-grants-2012_09
Patent number
US08263627B2

Reaction notes

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