Cyanuric chloride → HCID 67965001, compound

HRID 1254017Notes

Reaction equation

HRID 1254017 reaction equation
[C:1]([C:4]1[N:8]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[N:7]=[C:6]2[CH2:17][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][C:5]=12)(=O)[NH2:2].N1C(Cl)=NC(Cl)=NC=1Cl>CN(C=O)C>[C:1]([C:4]1[N:8]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[N:7]=[C:6]2[CH2:17][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][C:5]=12)#[N:2]

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 69929300HCID 69929300, compound

Product 1

HCID 67965001HCID 67965001, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of the product obtained in Step D (500 mg, 1.307 mmol) in DMF (10 mL) was added cyanuric chloride (482 mg, 2.61 mmol). The resulting mixture was stirred at RT under N2 overnight, quenched with saturated NaHCO3 and extracted with EtOAc (2×100 mL). The organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography on a silica gel Biotage 40S® column, eluting with 0 to 20% ethyl acetate in hexanes to give the title compound as a colorless gum. LC-MS: 265.1 (M-Boc).

Workup

  1. customquenched with saturated NaHCO3
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on a silica gel Biotage 40S® column
  7. washeluting with 0 to 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-702e141badb048768e4c12711412464c
Source dataset
uspto-grants-2013_06
Patent number
US08455533B2

Reaction notes

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