Chlorotrimethylsilane → HCID 21995562, compound

HRID 1603801Notes

Reaction equation

HRID 1603801 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][S:8]([C:11]2[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=2)(=[O:10])=[O:9])[CH:2]=1.Cl[Si](C)(C)C.[C:23](C1NC=CN=1)(C1NC=CN=1)=[O:24].[CH3:35][O:36][C:37]1[CH:38]=[C:39]2[C:43](=[CH:44][C:45]=1[C:46]([F:49])([F:48])[F:47])[NH:42][CH2:41][CH2:40]2>C(Cl)(Cl)Cl.O.CN(C)C=O.C(N(CC)CC)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][S:8]([C:11]2[CH:12]=[C:13]([NH:17][C:23]([N:42]3[C:43]4[C:39](=[CH:38][C:37]([O:36][CH3:35])=[C:45]([C:46]([F:49])([F:47])[F:48])[CH:44]=4)[CH2:40][CH2:41]3)=[O:24])[CH:14]=[CH:15][CH:16]=2)(=[O:10])=[O:9])[CH:2]=1

Participants

9

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 112067135-Methoxy-6-(trifluoromethyl)indolineHCID 16792745HCID 16792745, compound

Product 1

HCID 21995562HCID 21995562, compoundYield 60.9%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 3-(pyrid-3-ylaminosulphonyl)-aminobenzene (D39) (0.5 g, 2 mmol) in chloroform (40 ml) was treated with triethylamine (5 ml) and chlorotrimethylsilane (5 ml). The solution was evaporated to dryness, and the residue dissolved in dichloromethane (20 ml). Carbonyl diimidazole (0.32 g, 2 mmol) was added and after 1 h the reaction mixture was evaporated to dryness. Dimethylformamide (20 ml) and 5-methoxy-6-trifluoromethyl indoline (0.43 g, 2 mmol) was added, and the mixture heated to 100° C. for 2 h. The cooled solution was diluted with water (60 ml). Filtration and drying afforded a brown solid (0.6 g). Chromatography, eluting with 0-5% methanol in ethyl acetate afforded the product as a white solid (0.26 g, 26%), m.p. >215° C.

Workup

  1. customThe solution was evaporated to dryness
  2. dissolutionthe residue dissolved in dichloromethane (20 ml)
  3. customwas evaporated to dryness
  4. filtrationFiltration
  5. customdrying

Sources & evidence

ORD record
ord-4e35548660704fc9a8ad771b01aebeb0
Source dataset
uspto-grants-1999_11
Patent number
US05990133

Reaction notes

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