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Water → 1-(4,6-Di-pyridin-3-yl-thiazolo[5,4-c]pyridin-2-yl)-3-ethyl-urea

HRID 447067
Notes
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Reaction equation

HRID 447067 reaction equation
Br[C:2]1[C:7]2[S:8][C:9]([NH:11][C:12]([NH:14][CH2:15][CH3:16])=[O:13])=[N:10][C:6]=2[CH:5]=[C:4](Br)[N:3]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20](B(O)O)[CH:19]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>CN(C=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:2]2[C:7]3[S:8][C:9]([NH:11][C:12]([NH:14][CH2:15][CH3:16])=[O:13])=[N:10][C:6]=3[CH:5]=[C:4]([C:7]3[CH:2]=[N:3][CH:4]=[CH:5][CH:6]=3)[N:3]=2)[CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 27343783-Pyridinylboronic acidHCID 580332371-(4,6-Dibromothiazolo[5,4-c]pyridin-2-yl)-3-ethylurea

Product 1

HCID 426229601-(4,6-Di-pyridin-3-yl-thiazolo[5,4-c]pyridin-2-yl)-3-ethyl-ureaYield 46.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-(4,6-dibromo-thiazolo[5,4-c]pyridin-2-yl)-3-ethyl-urea (0.07 g, 0.17 mmol) in DMF:H2O (3:1, 4 mL) was added pyridine-3-boronic acid (0.08 g, 0.68 mmol) and potassium phosphate tribasic (0.09 g, 0.43 mmol) at room temperature under nitrogen atmosphere. The reaction mixture was degassed by bubbling nitrogen for 15-20 min followed by addition of Pd(PPh3)4 (0.04 g, 0.07 mmol). The resulting solution was again degassed for 15-20 min followed by heating up to 90° C. overnight. After completion of reaction (TLC monitoring), the reaction mixture was cooled, water was added and extracted with ethyl acetate, dried over Na2SO4 and evaporated to dryness under high vacuum. The crude residue was purified by Prep HPLC to get the desired product (0.015 g, 23%).

Workup

  1. customThe reaction mixture was degassed
  2. customby bubbling nitrogen for 15-20 min
  3. customThe resulting solution was again degassed for 15-20 min
  4. customAfter completion of reaction (TLC monitoring)
  5. temperaturethe reaction mixture was cooled
  6. extractionextracted with ethyl acetate
  7. dry with materialdried over Na2SO4
  8. customevaporated to dryness under high vacuum
  9. customThe crude residue was purified by Prep HPLC

Sources & evidence

ORD record
ord-af33ba7c571440c392724a530bbac7e4
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08481544B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes