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Cesium carbonate → N-(4-(3-(Tetrahydrofuran-3-YL)pyridin-2-yloxy)phenyl)benzo[D]thiazol-2-amine

HRID 1880160
Notes
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Reaction equation

HRID 1880160 reaction equation
F[C:2]1[C:7]([CH:8]2[CH2:12][CH2:11][O:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[S:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[NH:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[O:10]1[CH2:11][CH2:12][CH:8]([C:7]2[C:2]([O:29][C:26]3[CH:25]=[CH:24][C:23]([NH:22][C:14]4[S:13][C:17]5[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=5[N:15]=4)=[CH:28][CH:27]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH2:9]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 593268134-(Benzo[d]thiazol-2-ylamino)phenolHCID 593272332-Fluoro-3-(tetrahydrofuran-3-YL)pyridine

Product 1

HCID 59327054N-(4-(3-(Tetrahydrofuran-3-YL)pyridin-2-yloxy)phenyl)benzo[D]thiazol-2-amine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent
HCID 962
Water
Solvent

Conditions

Temperature
100 °C

Procedure

A glass microwave reaction vessel was charged with 2-fluoro-3-(tetrahydrofuran-3-yl)pyridine (1.00 g, 5.98 mmol), 4-(benzo[d]thiazol-2-ylamino)phenol (1.56 g, 6.44 mmol) and cesium carbonate (4.88 g, 14.98 mmol) in DMSO (10 mL). The reaction mixture was sealed under argon and was heated thermally at 100° C. for 24 h. The reaction was cooled to rt and diluted with water. The product turned into a gum and the aqueous solution was decanted. The gum was stirred over MeOH for 1 h resulting in a precipitate that was filtered, washed with MeOH and dried in vacuo to give the title compound as a white crystalline solid. MS (ESI, pos. ion) m/z: 389.9 (M+1). IC50 (uM) +++++.

Workup

  1. customA glass microwave reaction vessel
  2. customThe reaction mixture was sealed under argon
  3. temperatureThe reaction was cooled to rt
  4. customthe aqueous solution was decanted
  5. customresulting in a precipitate that
  6. filtrationwas filtered
  7. washwashed with MeOH
  8. customdried in vacuo

Sources & evidence

ORD record
ord-a3c40f1bc9434b54bf2415c7cefd2d54
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08318718B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes