1,4-Dioxane hydrochloride → 2-(4-Chloro-2-oxo-1,2-dihydro-pyridin-3-yl)-7-methyl-3H-benzimidazole-5-carbonitrile

HRID 1793703

Reaction equation

HRID 1793703 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8]C)[C:3]=1[C:10]1[NH:11][C:12]2[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[C:15]([CH3:21])[C:13]=2[N:14]=1.O1CCOCC1.[ClH:28]>>[Cl:28][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[C:10]1[NH:11][C:12]2[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[C:15]([CH3:21])[C:13]=2[N:14]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 220210132-(4-Iodo-2-methoxy-pyridin-3-yl)-7-methyl-3H-benzimidazole-5-carbonitrile

Product 1

HCID 1356816422-(4-Chloro-2-oxo-1,2-dihydro-pyridin-3-yl)-7-methyl-3H-benzimidazole-5-carbonitrile

Conditions

Temperature
80 °C

Procedure

A suspension of 2-(4-iodo-2-methoxy-pyridin-3-yl)-7-methyl-3H-benzimidazole-5-carbonitrile (1.8 g, 4.63 mmol) in 4 M HCl dioxane (40 mL) was heated to 80° C. for 6 h and cooled to room temperature. The precipitate was filtered and dried. The crude product (1.08 g, 82%) was used for the next step without purification. LRMS (neg. ESI, (M−H)−) m/z 283.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipitate was filtered
  3. customdried
  4. customThe crude product (1.08 g, 82%) was used for the next step without purification

Sources & evidence

ORD record
ord-e9b129fd196c4375af69d56e4306eba2
Source dataset
uspto-grants-2006_07
Patent number
US07081454B2

Linked notes

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