Cyanuric chloride → HCID 11045887, compound

HRID 496020Notes

Reaction equation

HRID 496020 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5]([Cl:6])=[N:4][C:2]=1Cl.[C:10]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C>C(Cl)Cl>[C:13]([O:12][C:10]([N:17]1[CH2:22][CH2:21][N:20]([C:2]2[N:1]=[C:8]([Cl:9])[N:7]=[C:5]([Cl:6])[N:4]=2)[CH2:19][CH2:18]1)=[O:11])([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 7954Cyanuric chloride2×HCID 88675Proton spongeHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 11045887HCID 11045887, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 5.3 g (29.0 mmol) of cyanuric chloride in 200 mL of DCM was cooled to −10° C. A solution of 5.3 g (29.0 mmol, 1.0 equiv.) of N-BOC piperazine and 6.2 g (29.0 mmo, 1.0 equiv.) of Proton Sponge® in 40 mL of DCM was then added dropwise over 20 min. to the cyanuric chloride solution. The resulting mixture was allowed to warm to RT and stirred 2 h. The reaction mixture was quenched by pouring into 150 mL of a 5% aqueous citric acid solution and extracted with DCM (2×100 mL). The organic layers were combined, dried (MgSO4), and concentrated in vacuo. Purification of the residue by silica gel flash column chromatography eluting with hexanes/EtOAc 3:1 afforded 8.6 g (85%) of the title compound as a white solid: 1H NMR (CDCl3, 400 MHz) δ 3.86 (m, 4H), 3.49 (m, 4H), 1.42 (s, 9H); low resolution MS (ES+) m/e 335 (MH+);TLC (hexanes/EtOAc 20:1) Rf=0.10. Intermediate 2: tert-butyl-4-{4-chloro-6-[[3-(4-chlorophenyl)propyl](methyl)amino]-1,3,5-triazin-2-yl}-1-piperazinecarboxylate.

Workup

  1. customThe reaction mixture was quenched
  2. additionby pouring into 150 mL of a 5% aqueous citric acid solution
  3. extractionextracted with DCM (2×100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by silica gel flash column chromatography
  7. washeluting with hexanes/EtOAc 3:1

Sources & evidence

ORD record
ord-09590e8a538943b2acf8607b1f12c93e
Source dataset
uspto-grants-2005_09
Patent number
US06943162B2

Reaction notes

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