[3-(2,4-dihydroxy-5-isopropyl-phenyl)-5-ethylcarbamoyl-3H-[1,2,3]triazol-4-yl]-(4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester → 1-(2,4-dihydroxy-5-isopropyl-phenyl)-5-(4-morpholin-4-yl-phenylamino)-1H-[1,2,3]triazole-4-carboxylic acid ethylamide

HRID 623686Notes

Reaction equation

HRID 623686 reaction equation
C(OC(=O)[N:7]([C:20]1[N:21]([C:30]2[CH:35]=[C:34]([CH:36]([CH3:38])[CH3:37])[C:33]([OH:39])=[CH:32][C:31]=2[OH:40])[N:22]=[N:23][C:24]=1[C:25](=[O:29])[NH:26][CH2:27][CH3:28])[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>[CH2:27]([NH:26][C:25]([C:24]1[N:23]=[N:22][N:21]([C:30]2[CH:35]=[C:34]([CH:36]([CH3:37])[CH3:38])[C:33]([OH:39])=[CH:32][C:31]=2[OH:40])[C:20]=1[NH:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)=[CH:10][CH:9]=1)=[O:29])[CH3:28]

Participants

3

Reactant 1

HCID 117678002[3-(2,4-dihydroxy-5-isopropyl-phenyl)-5-ethylcarbamoyl-3H-[1,2,3]triazol-4-yl]-(4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 574046081-(2,4-dihydroxy-5-isopropyl-phenyl)-5-(4-morpholin-4-yl-phenylamino)-1H-[1,2,3]triazole-4-carboxylic acid ethylamideYield 45%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of the intermediate from Step D in DCM/TFA (1/1, 2 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 a 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-9dce19a34d0648e883e25d390104dd15
Source dataset
uspto-grants-2016_04
Patent number
US09302998B2

Reaction notes

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