Cyanuric chloride → HCID 178478357, compound

HRID 1961376Notes

Reaction equation

HRID 1961376 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].C(N(C(C)C)CC)(C)C.[CH:19]1([C:22]2[CH:26]=[C:25]([NH2:27])[NH:24][N:23]=2)[CH2:21][CH2:20]1>C1COCC1.C(O)(C)C>[Cl:9][C:8]1[N:1]=[C:2]([Cl:3])[N:4]=[C:5]([NH:27][C:25]2[NH:24][N:23]=[C:22]([CH:19]3[CH2:21][CH2:20]3)[CH:26]=2)[N:7]=1

Participants

6

Reactant 3

HCID 7954Cyanuric chlorideHCID 81531DiisopropylethylamineHCID 178507266HCID 178507266, compound

Product 1

HCID 178478357HCID 178478357, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of cyanuric chloride (5 g, 27.1 mmol) in THF (40 mL) were added diisopropylethylamine (7.1 mL, 40.6 mmol) and 3-cyclopropyl-1H-pyrazol-5-amine (4.0 g, 32.5 mmol) in isopropyl alcohol (40 mL) at 0° C. over 30 minutes. The reaction mixture was stirred at room temperature overnight. The crude reaction solution was used for the next step without purification. A small amount was purified by Biotage (0-50% EtOAc/Hexane, 1 L). 1H NMR (DMSO, 400 MHz) δ 11.33 (s, NH), 6.19 (s, 1H), 3.83 (br s, NH), 1.88-1.95 (m, 1H), 0.93-0.96 (m, 2H), 0.68-0.70 (m, 2H). LC/MS [M+H]+: 271/273; Ret time (Method F): 3.00 min.

Workup

  1. customThe crude reaction solution
  2. customwas used for the next step without purification
  3. customA small amount was purified by Biotage (0-50% EtOAc/Hexane, 1 L)
  4. custom3.00 min.

Sources & evidence

ORD record
ord-b0d8214d8b4b4844a4c5eb0517e800c7
Source dataset
uspto-grants-2013_04
Patent number
US08415340B2

Reaction notes

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