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Isocyanate → 1-[2-(3-Pyridyl)-thiazol-4-yl carbamoyl]-5-methoxy-6-trifluoromethylindoline

HRID 989198
Notes
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Reaction equation

HRID 989198 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][CH:9]=[C:10](C(N=[N+]=[N-])=O)[N:11]=2)[CH:2]=1.[N-:17]=[C:18]=[O:19].[CH3:20][O:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][C:30]=1[C:31]([F:34])([F:33])[F:32])[NH:27][CH2:26][CH2:25]2>C1(C)C=CC=CC=1.ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][CH:9]=[C:10]([NH:17][C:18]([N:27]3[C:28]4[C:24](=[CH:23][C:22]([O:21][CH3:20])=[C:30]([C:31]([F:33])([F:34])[F:32])[CH:29]=4)[CH2:25][CH2:26]3)=[O:19])[N:11]=2)[CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 105034IsocyanateHCID 112067135-Methoxy-6-(trifluoromethyl)indolineHCID 187718652-(3-Pyridinyl)-4-thiazolylcarbonylazide

Product 1

HCID 232181211-[2-(3-Pyridyl)-thiazol-4-yl carbamoyl]-5-methoxy-6-trifluoromethylindolineYield 15%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent
HCID 6344DichloromethaneSolvent

Procedure

A solution of acyl azide D15) (370 mg, 1.6 mmol) in toluene (5 ml) was heated to reflux for 0.25 h. After cooling to room temperature, the solution of the isocyanate was added to a solution of 5-methoxy-6-trifluoromethyl indoline (0.35 g, 1.6 mmol) in dichloromethane (10 ml). Filtration and drying afforded the title compound as a white solid (100 mg, 15%), m.p.>200° C.

Workup

  1. temperatureto reflux for 0.25 h
  2. filtrationFiltration
  3. customdrying

Sources & evidence

ORD record
ord-e5c1ee44e76e44ee95d73c41d69fa348
Source dataset
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06638953B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes