Acetyl chloride → HCID 178474849, compound

HRID 1852543Notes

Reaction equation

HRID 1852543 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=[N:17]3)[CH:13]=[CH:12][N:11]=2)[CH2:5][CH2:4]1.[C:25](Cl)(=[O:27])[CH3:26]>C(Cl)Cl.O>[N:16]1([C:14]2[CH:13]=[CH:12][N:11]=[C:10]([NH:9][C@H:6]3[CH2:5][CH2:4][C@H:3]([CH2:2][NH:1][C:25](=[O:27])[CH3:26])[CH2:8][CH2:7]3)[N:15]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[N:17]1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 178511278HCID 178511278, compound

Product 1

HCID 178474849HCID 178474849, compoundYield 14.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

TEA (52 μL, 0.37 mmol) was added, under nitrogen atmosphere, to a solution of trans-(4-aminomethyl-cyclohexyl)-(4-benzotriazol-1-yl-pyrimidin-2-yl)-amine (60 mg, 0.185 mmol) in DCM (3 mL). The mixture was cooled to −78° C. and acetyl chloride (13.2 μL, 0.185 mmol) was added. The reaction mixture was stirred at RT overnight; it was then poured in water and extracted 3 times with a mixture of isopropanol and chloroform. The combined organic extracts were dried over Na2SO4, filtered and the solvent was evaporated under reduced pressure. The crude residue was purified via preparative TLC to give 10 mg of trans-N-[4-(4-benzotriazol-1-yl-pyrimidin-2-ylamino)-cyclohexylmethyl]-acetamide. 1H NMR (400 MHz, CDCl3) δ ppm 8.55 (1 H, d, J=8.19 Hz), 8.41 (1 H, d, J=5.14 Hz), 8.12 (1 H, d, J=8.19 Hz), 7.57-7.67 (1 H, m), 7.42-7.51 (2 H, m), 7.16-7.24 (0.3 H, m), 5.55-5.64 (0.7 H, m), 5.18-5.43 (1 H, m), 3.80-3.93 (1 H, m), 3.11-3.25 (2 H, m), 2.27 (1 H, s), 2.19-2.35 (2 H, m), 2.00 (2 H, s), 1.85-1.95 (2 H, m), 1.50-1.63 (1 H, m), 1.11-1.37 (4 H, m).

Workup

  1. extractionextracted 3 times
  2. additionwith a mixture of isopropanol and chloroform
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe crude residue was purified via preparative TLC

Sources & evidence

ORD record
ord-f36e6e92ca554b9c8c123f9d77febc9d
Source dataset
uspto-grants-2015_02
Patent number
US08962622B2

Reaction notes

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