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

HRID 1977760Notes

Reaction equation

HRID 1977760 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

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 1140TolueneSolventHCID 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-b5b2dd94ef5b4356b1f64868ffd7c2d5
Source dataset
uspto-grants-2001_05
Patent number
US06235758B1

Reaction notes

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