Pyridine → HCID 54258805, compound

HRID 1433032Notes

Reaction equation

HRID 1433032 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].Cl.Cl[NH:32][CH:33]=O.[N:35]1C=CC=CC=1>>[Cl:28][C:25]1[CH:26]=[CH:27][C:21]2[N:20]=[C:19]([CH2:18][CH:15]3[CH2:16][CH2:17][N:12]([CH2:11][C:9]4[CH:10]=[C:3]5[C:4]([C:5]([NH2:35])=[N:6][C:33]([NH2:32])=[N:2]5)=[CH:7][CH:8]=4)[C:13](=[O:29])[CH2:14]3)[NH:23][C:22]=2[CH:24]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 69027088HCID 69027088, compoundHCID 86592550HCID 86592550, compound

Product 1

HCID 54258805HCID 54258805, compoundYield 45%

Conditions

Temperature
200 °C

Procedure

2-Amino-4-[4-(6-chloro-1H-benzoimidazol-2-ylmethyl)-2-oxo-piperidin-1-ylmethyl]-benzonitrile hydrochloric acid salt (70 mg, 0.15 mmol), EXAMPLE 814, Part E, pyridine (1.0 mL) and freshly made chloroformamide hydrochloride (150 mg, 1.33 mmol) are placed in a sealed tube and heated to 200° C. The resulting mixture is heated for twenty four hours. The crude reaction mixture is directly purified by reverse phase HPLC (0-50% ACN/H2O). The product (53 mg, 45% yield) is isolated as a tanish solid. C22H22ClN7O MS m/z: 436,438. Anal. calcd. for C22H22ClN7O: C, 43.23; H, 3.24; N, 12.60. Found: C, 43.16; H, 3.44; N, 13.40.

Workup

  1. temperatureThe resulting mixture is heated for twenty four hours
  2. customThe crude reaction mixture
  3. customis directly purified by reverse phase HPLC (0-50% ACN/H2O)

Sources & evidence

ORD record
ord-6b7bc7e623e1455794e9e530988fae8a
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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