Catechol → HCID 71529484, compound

HRID 1520353Notes

Reaction equation

HRID 1520353 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[N:13]=[C:12]2[NH:25][C:26]1[S:27][CH:28]=[C:29]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)[N:30]=1)C1C=CC=CC=1.C1(C(=CC=CC=1)O)O.COC.CS(O)(=O)=O.C([O-])(O)=O.[Na+]>O>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([C:29]2[N:30]=[C:26]([NH:25][C:12]3[C:11]4[C:16](=[CH:17][CH:18]=[C:9]([OH:8])[CH:10]=4)[N:15]=[C:14]([C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)[N:13]=3)[S:27][CH:28]=2)=[CH:32][CH:33]=1

Participants

7

Reactant 5

HCID 289CatecholHCID 6395Methanesulfonic AcidHCID 8254Dimethyl EtherHCID 516892Sodium BicarbonateHCID 86677077HCID 86677077, compound

Product 1

HCID 71529484HCID 71529484, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of N-(6-(benzyloxy)-2-(pyridin-3-yl)quinazolin-4-yl)-4-(4-chlorophenyl)thiazol-2-amine and catechol, dimethyl ether (0.16 g, 1.15 mmol) was added methanesulfonic acid (4.0 mL). The mixture was stirred for 1 hr and was then poured into water. The slurry was added to a stirring sat. NaHCO3(aq), solution slowly and allowed to stir for 30 min. The precipitate was filtered to give a brown solid which was washed with methanol to give 4-(4-(4-chlorophenyl)thiazol-2-ylamino)-2-(pyridin-3-yl)quinazolin-6-ol (0.23 g, 91.0%).

Workup

  1. stirringto stir for 30 min
  2. filtrationThe precipitate was filtered
  3. customto give a brown solid which
  4. washwas washed with methanol

Sources & evidence

ORD record
ord-25147c0eda0345cda1fd3b1c92c2a6df
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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