Acetic Acid → (R)-2-(5-bromo-4-cyano-2-fluorophenylamino)-3-(4-(pyridin-4-yl)phenyl)propanamide

HRID 84897Notes

Reaction equation

HRID 84897 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].[NH2:12][C:13](=[O:36])[C@H:14]([NH:28]C(=O)OC(C)(C)C)[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[CH:18][CH:17]=1.CCN(C(C)C)C(C)C.CC(O)=O>CS(C)=O>[Br:1][C:2]1[C:3]([C:4]#[N:5])=[CH:6][C:7]([F:11])=[C:8]([NH:28][C@H:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=3)=[CH:18][CH:17]=2)[C:13]([NH2:12])=[O:36])[CH:9]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 192612772-Bromo-4,5-difluorobenzonitrileHCID 67509306HCID 67509306, compound

Product 1

HCID 67508174(R)-2-(5-bromo-4-cyano-2-fluorophenylamino)-3-(4-(pyridin-4-yl)phenyl)propanamideYield 47.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-bromo-4,5-difluorobenzonitrile (85 mg, 0.390 mmol), (R)-tert-butyl 1-amino-1-oxo-3-(4-(pyridin-4-yl)phenyl)propan-2-ylcarbamate (72 mg, 0.299 mmol) and DIEA (0.200 mL, 1.15 mmol) in DMSO (3 mL) was stirred at 120 C for 18 h. HOAc (0.5 mL) was added. The mixture was purified by HPLC to give (R)-2-(5-bromo-4-cyano-2-fluorophenylamino)-3-(4-(pyridin-4-yl)phenyl)propanamide (62 mg).

Workup

  1. customThe mixture was purified by HPLC

Sources & evidence

ORD record
ord-fe1926292a63415a934220de9c421eeb
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Reaction notes

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