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2-Cyclopenten-1-one → 3-(2-(4-(Benzo[D]thiazol-2-ylamino)phenoxy)pyridin-3-YL)cyclopent-2-enone

HRID 410300
Notes
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Reaction equation

HRID 410300 reaction equation
Br[C:2]1[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[S:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:25]1(=[O:30])[CH2:29][CH2:28][CH:27]=[CH:26]1.CN(C1CCCCC1)C1CCCCC1>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[S:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[NH:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:3]2[C:2]([C:27]3[CH2:28][CH2:29][C:25](=[O:30])[CH:26]=3)=[CH:7][CH:6]=[CH:5][N:4]=2)=[CH:10][CH:11]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 135882-Cyclopenten-1-oneHCID 24210N-Methyl dicyclohexylamineHCID 59326883N-(4-(3-bromopyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine

Product 1

HCID 462148733-(2-(4-(Benzo[D]thiazol-2-ylamino)phenoxy)pyridin-3-YL)cyclopent-2-enone

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compound
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of N-(4-(3-bromopyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine (600 mg, 1.506 mmol), 2-cyclopenten-1-one (0.609 mL, 7.53 mmol), n-methyldicyclohexylamine (0.959 mL, 4.52 mmol) and bis(tri-tert-butylphosphine)palladium (0) (77 mg, 0.151 mmol) in Dioxane (4 mL) was capped, degassed and backfilled with argon. The reaction was heated to 90° C. After 6 h, the reaction was heated to 110° C. After 36 h, the reaction was cooled to 23° C., diluted with EtOAc (150 mL) and washed with water (100 mL) and brine (100 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluant: 0.5-3% methanol/dichloromethane), affording the product as a yellow solid. MS (ESI, pos. ion) m/z: 400.1 (M+1).

Workup

  1. customdegassed
  2. temperaturethe reaction was heated to 110° C
  3. waitAfter 36 h
  4. temperaturethe reaction was cooled to 23° C.
  5. additiondiluted with EtOAc (150 mL)
  6. washwashed with water (100 mL) and brine (100 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. custompurified by silica gel chromatography (eluant: 0.5-3% methanol/dichloromethane)

Sources & evidence

ORD record
ord-fc4f7fdfe855417bac3e67455f19af18
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08759532B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes