tert-butyl 1-(2,4-dihydroxy-5-isopropylphenyl)-1H-1,2,3-triazol-5-yl(4-morpholinobenzyl)carbamate → 4-Isopropyl-6-[5-(4-morpholin-4-yl-benzylamino)-[1,2,3]triazol-1-yl]-benzene-1,3-diol

HRID 623681Notes

Reaction equation

HRID 623681 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([CH:9]([CH3:11])[CH3:10])=[CH:4][C:3]=1[N:12]1[C:16]([N:17]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[CH:28][CH:27]=2)C(=O)OC(C)(C)C)=[CH:15][N:14]=[N:13]1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH:9]([C:5]1[CH:4]=[C:3]([N:12]2[C:16]([NH:17][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([N:32]4[CH2:33][CH2:34][O:35][CH2:36][CH2:37]4)=[CH:30][CH:31]=3)=[CH:15][N:14]=[N:13]2)[C:2]([OH:1])=[CH:7][C:6]=1[OH:8])([CH3:11])[CH3:10]

Participants

3

Reactant 1

HCID 117678674tert-butyl 1-(2,4-dihydroxy-5-isopropylphenyl)-1H-1,2,3-triazol-5-yl(4-morpholinobenzyl)carbamate

Product 1

HCID 574046074-Isopropyl-6-[5-(4-morpholin-4-yl-benzylamino)-[1,2,3]triazol-1-yl]-benzene-1,3-diolYield 50%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of the intermediate from Step D 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-a6543491e2134c5fab865797e63fae41
Source dataset
uspto-grants-2016_04
Patent number
US09302998B2

Reaction notes

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