1,2-Dichloroethane → HCID 52932105, compound

HRID 877371Notes

Reaction equation

HRID 877371 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=O)=[CH:3][CH:2]=1.[Cl-].[Cl-].[NH3+:19][C@@H:20]([C:22]1[S:23][C:24]([CH3:27])=[CH:25][NH+:26]=1)[CH3:21].C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C>CN(C=O)C>[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:2]=[CH:3][C:4]([CH2:7][C:8]([NH:19][C@@H:20]([C:22]2[S:23][C:24]([CH3:27])=[CH:25][N:26]=2)[CH3:21])=[O:10])=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 3332FelbinacHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 86668965HCID 86668965, compound

Product 1

HCID 52932105HCID 52932105, compoundYield 866.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.05 g (0.24 mmol) 1,1′-biphenyl-4-ylacetic acid in 0.50 ml DMF was added 0.05 g (0.24 mmol) 2-[(1R)-1-ammonioethyl]-5-methyl-1,3-thiazol-3-ium dichloride, 0.04 g (0.31 mmol) HOAT, 0.60 g (0.31 mmol) EDC, and 0.12 mL (0.71 mmol) DIEA. After 24 h at room temperature, the reaction mixture was purified by preparative HPLC (5->95% CH3CN/H2O over 15 min, 0.05% added TFA, C18) to afford 0.70 g (86%) 2-(biphenyl-4-yl)-N-[(1R)-1-(5-methyl-1,3-thiazol-2-yl)ethyl]acetamide. 1H NMR (CDCl3, 400 MHz) 7.59 (m, 4H), 7.44 (m, 2H), 7.35 (m, 4H), 6.55 (br d, 1H, J=7.32 Hz), 5.43 (m, 1H), 3.65 (s, 2H), 2.43 (s, 3H), 1.55 (d, 3H, J=6.96 Hz). HRMS (ES) [M+1]+ calcd for C20H21N2OS: 337.1375. Found: 337.1368.

Workup

  1. customthe reaction mixture was purified by preparative HPLC (5->95% CH3CN/H2O over 15 min, 0.05% added TFA, C18)

Sources & evidence

ORD record
ord-c0bef195a94845a7a18497841e51b07d
Source dataset
uspto-grants-2015_03
Patent number
US08987310B2

Reaction notes

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