[3-(2,4-dihydroxy-5-isopropyl-phenyl)-3H-[1,2,3]triazol-4-yl]-(4-morpholin-4-yl-phenyl)-carbamic acid t-butyl ester → 4-Isopropyl-6-[5-(4-morpholin-4-yl-phenylamino)-[1,2,3]triazol-1-yl]-benzene-1,3-diol

HRID 623676Notes

Reaction equation

HRID 623676 reaction equation
C(OC(=O)[N:7]([C:20]1[N:21]([C:25]2[CH:30]=[C:29]([CH:31]([CH3:33])[CH3:32])[C:28]([OH:34])=[CH:27][C:26]=2[OH:35])[N:22]=[N:23][CH:24]=1)[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH:31]([C:29]1[CH:30]=[C:25]([N:21]2[C:20]([NH:7][C:8]3[CH:9]=[CH:10][C:11]([N:14]4[CH2:15][CH2:16][O:17][CH2:18][CH2:19]4)=[CH:12][CH:13]=3)=[CH:24][N:23]=[N:22]2)[C:26]([OH:35])=[CH:27][C:28]=1[OH:34])([CH3:33])[CH3:32]

Participants

3

Reactant 1

HCID 131735186[3-(2,4-dihydroxy-5-isopropyl-phenyl)-3H-[1,2,3]triazol-4-yl]-(4-morpholin-4-yl-phenyl)-carbamic acid t-butyl ester

Product 1

HCID 574046064-Isopropyl-6-[5-(4-morpholin-4-yl-phenylamino)-[1,2,3]triazol-1-yl]-benzene-1,3-diolYield 45%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of the intermediate from Step E in DCM/TFA (1/1 5 ml) was stirred for 12 hours at RT. The reaction mixture was concentrated under reduced pressure and the crude reaction mixture was purified by column chromatography (DCM/MeOH: 95/5). The title compound was obtained as slightly brown solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe crude reaction mixture
  3. customwas purified by column chromatography (DCM/MeOH: 95/5)

Sources & evidence

ORD record
ord-6104a9e4cc994815ba91308fc49594dd
Source dataset
uspto-grants-2016_04
Patent number
US09302998B2

Reaction notes

Loading…