Triethylamine → 1-[1-[(6-Chloroimidazo[1,2-a]pyridin-2-yl)methyl]-4-piperidinyl]-1,3-dihydro-2H-benzimidazol-2-one

HRID 1416249Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11]Cl)[N:10]=2)[CH:7]=1.[O:13]=[C:14]1[N:18]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[C:17]2[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=2[NH:15]1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:22]3[CH2:21][CH2:20][CH:19]([N:18]4[C:17]5[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=5[NH:15][C:14]4=[O:13])[CH2:24][CH2:23]3)[N:10]=2)[CH:7]=1

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of 6-chloro-2-(chloromethyl)imidazo[1,2-a]pyridine (Example 4, Step 1: 0.186 g), 4-(2-keto-1-benzimidazolinyl)piperidine (Aldrich; 0.201 g), triethylamine (0.094 g), and dichloromethane (4 mL) is stirred at 45° C. for 20 h, after which time the mixture is cooled. Dichloromethane and aqueous sodium bicarbonate are added and the solids collected and dried. Additional material is obtained by concentration of the organic layer. Crystallization from methanol/dichloromethane/hexane gives 0.123 g of the title compound; mp 210-211 (decomp)°C; IR (mineral oil) 1695, 1486, 1338, 736, 1074 cm-1. 1H NMR (DMSOd6) δ1.63, 2.19, 2.38, 3.08, 3.66, 4.12, 6.96, 7.23, 7.54, 7.87, 8.80, 10.84.

Workup

temperatureafter which time the mixture is cooled
customthe solids collected
customdried
customAdditional material is obtained by concentration of the organic layer
customCrystallization from methanol/dichloromethane/hexane

Sources & evidence

ORD record: ord-c435aeac15274a65895b7035f8e25c21
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05912246

Reaction notes

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