Water → HCID 9858633, compound

HRID 347911Notes

Reaction equation

HRID 347911 reaction equation
N1C(Cl)=NC(Cl)=NC=1Cl.[O:10]=[C:11]1[N:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:15]2[S:23][C:24]([C:32]([NH2:34])=O)=[C:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:14]=2[CH:13]=[CH:12]1.O>CN(C=O)C>[O:10]=[C:11]1[N:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:15]2[S:23][C:24]([C:32]#[N:34])=[C:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:14]=2[CH:13]=[CH:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 7954Cyanuric chloride2×HCID 21083990HCID 21083990, compound

Product 1

HCID 9858633HCID 9858633, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of cyanuric chloride (28 mg, 0.15 mmol) and the compound of Example 75 (52 mg, 0.15 mmol) in DMF (1.5 mL) was heated at 110° for 18 h. Two further portions of cyanuric chloride (14 mg, 0.075 mmol) were added and heating continued for a further 26 h. Water was added and the precipitate filtered off, washed with water and dried. The crude product was purified by column chromatography on silica (1% THF in DCM) to give the title compound as a white solid (35 mg, 71%). δH (DMSO-d6) 7.78 (1H, d, J 9.6 Hz), 7.71–7.67 (1H, m), 7.66–7.64 (1H, m), 7.64–7.59 (7H, m), 7.59–7.58 (1H, m), 6.67 (1H, d, J 9.6 Hz). LCMS (ES+) RT 3.65 minutes, 329 (M+H)+.

Workup

  1. temperatureheating
  2. filtrationthe precipitate filtered off
  3. washwashed with water
  4. customdried
  5. customThe crude product was purified by column chromatography on silica (1% THF in DCM)

Sources & evidence

ORD record
ord-a59307fadada455d8092571db613b032
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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