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Cesium carbonate → 4-(3-(4-(Benzo[D]thiazol-2-ylamino)phenoxy)pyrazin-2-YL)tetrahydro-2H-pyran-4-OL

HRID 2191982
Notes
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Reaction equation

HRID 2191982 reaction equation
F[C:2]1[C:3]([C:8]2([OH:14])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.[S:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[NH:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.C(Cl)Cl>[S:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[NH:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:2]2[C:3]([C:8]3([OH:14])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)=[N:4][CH:5]=[CH:6][N:7]=2)=[CH:27][CH:26]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 593268134-(Benzo[d]thiazol-2-ylamino)phenolHCID 593512304-(3-Fluoropyrazin-2-YL)tetrahydro-2H-pyran-4-OL

Product 1

HCID 593511974-(3-(4-(Benzo[D]thiazol-2-ylamino)phenoxy)pyrazin-2-YL)tetrahydro-2H-pyran-4-OL

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent
HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(3-fluoropyrazin-2-yl)tetrahydro-2H-pyran-4-ol (0.1 g, 0.505 mmol) in DMSO (1 mL) was added 4-(benzo[d]thiazol-2-ylamino)phenol (0.183 g, 0.757 mmol) and cesium carbonate (0.329 g, 1.009 mmol). The resulting mixture was heated to 80° C. overnight. Reaction mixture was diluted with DCM and washed with alternating washes of water and brine to remove DMSO. Purification by Biotage (0-10% MeOH/DCM) produced product. MS (ESI, pos. ion) m/z: 421.1 (M+1). IC50 (uM) +++++.

Workup

  1. customReaction mixture
  2. washwashed with alternating washes of water and brine
  3. customto remove DMSO
  4. customPurification by Biotage (0-10% MeOH/DCM)
  5. customproduced product

Sources & evidence

ORD record
ord-b1e86770a1d3462faa9374ea20d33b1d
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08329700B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes