Acetic Acid → HCID 69028266, compound

HRID 1433031Notes

Reaction equation

HRID 1433031 reaction equation
Cl.[NH2:2][C:3]1[CH:10]=[C:9]([CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][C:19]3[NH:23][C:22]4[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:21]=4[N:20]=3)[CH2:14][C:13]2=[O:29])[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[CH2:30]([N:32](CC)CC)C.C(O)(=O)C.N1C=CC=NN=1>C(O)C>[NH2:6][C:5]1[C:4]2[C:3](=[CH:10][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([CH2:18][C:19]4[NH:23][C:22]5[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:21]=5[N:20]=4)[CH2:14][C:13]3=[O:29])=[CH:8][CH:7]=2)[N:2]=[CH:30][N:32]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 1230471,2,3-TriazineHCID 69027088HCID 69027088, compound

Product 1

HCID 69028266HCID 69028266, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-Amino-4-[4-(6-chloro-1H-benzoimidazol-2-ylmethyl)-2-oxo-piperidin-1-ylmethyl]-benzonitrile hydrochloric acid salt (143 mg, 0.308 mmol), EXAMPLE 814, Part E, in 2 mL of ethanol is added triethylamine (0.05 mL, 0.366 mmol), glacial acetic acid (0.02 mL, 0.366 mmol) and triazine (15 mg, 0.183 mmol). The resulting mixture is refluxed overnight. The volatile solvents are removed on the rotovap, and the residue is purified by reverse phase HPLC (0-50% Acetonitrile/H2O). The desired product (110 mg, 55% yield) is isolated as a white powder with a melting point of 128-132 ° C. C22H21ClN6O MS m/z: 421, 423. Anal. calcd. for C22H21ClN6O: C, 48.12; H,3.57; N, 12.95. Found: C, 45.79; H, 3.68; N, 11.94. H NMR (CD3OD) δ: 8.67 (s, 1H); 8.31 (d, 1H, J=4.0 Hz); 7.83-7.55 (m, 5H); 4.93-4.73 (m, 2H); 3.48-3.42 (m, 2H); 3.31-3.21 (m, 2H); 2.71-2.58 (m, 2H); 2.43-2.33 (m, 1H); 2.07-2.01 (m, 1H); 1.82-1.69 (m, 1H).

Workup

  1. temperatureThe resulting mixture is refluxed overnight
  2. customThe volatile solvents are removed on the rotovap
  3. customthe residue is purified by reverse phase HPLC (0-50% Acetonitrile/H2O)

Sources & evidence

ORD record
ord-b60a8e0b5808412bb33d67f5f832183d
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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