Diisopropylethylamine → HCID 67514927, compound

HRID 84902Notes

Reaction equation

HRID 84902 reaction equation
[Br:1][C:2]1[CH:9]=[C:8](F)[C:7]([F:11])=[CH:6][C:3]=1[C:4]#[N:5].[N:12]1([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C@@H:24]([NH2:28])[C:25]([NH2:27])=[O:26])=[CH:19][CH:18]=2)[CH:16]=[CH:15][N:14]=[CH:13]1.CCN(C(C)C)C(C)C>CS(C)=O>[N:12]1([C:17]2[CH:18]=[CH:19][C:20]([CH2:23][C@@H:24]([NH:28][C:8]3[CH:9]=[C:2]([Br:1])[C:3]([C:4]#[N:5])=[CH:6][C:7]=3[F:11])[C:25]([NH2:27])=[O:26])=[CH:21][CH:22]=2)[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 192612772-Bromo-4,5-difluorobenzonitrileHCID 67516322(R)-3-(4-(1H-imidazol-1-yl)phenyl)-2-aminopropanamide

Product 1

HCID 67514927HCID 67514927, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-bromo-4,5-difluorobenzonitrile (100 mg, 0.458 mmol), ((R)-3-(4-(1H-imidazol-1-yl)phenyl)-2-aminopropanamide (100 mg, 0.434 mmol) and DIEA (0.100 mL, 0.575 mmol) in DMSO (3 mL) was stirred at 120 C for 18 h. The mixture was purified by HPLC to give (R)-3-(4-(1H-imidazol-1-yl)phenyl)-2-(5-bromo-4-cyano-2-fluorophenylamino)propanamide (59 mg).

Workup

  1. customThe mixture was purified by HPLC

Sources & evidence

ORD record
ord-81adb1500b354bd5b4cb95dc9e973c1f
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Reaction notes

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