Acetic Acid → HCID 18680815, compound

HRID 1699624Notes

Reaction equation

C(O)(=O)C.C(O)C.[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][NH:15][C:16](=[O:43])[C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24](=O)[CH3:25])=[C:19]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:31][CH:30]=2)[CH:18]=1.C(OCC)(=O)C>CCOCC>[CH2:36]([O:35][C:32]1[CH:33]=[CH:34][C:29]([CH2:28][N:27]2[C:19]3[CH:18]=[C:17]([C:16](=[O:43])[NH:15][CH2:14][C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][N:8]=4)[CH:22]=[CH:21][C:20]=3[N:23]=[C:24]2[CH3:25])=[CH:30][CH:31]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Acetic acid (4 ml) and ethanol (8 ml) are added to an N-(2-pyridylmethyl)-4-acetylamino-3-(4-benzyloxybenzylamino)benzamide (0.434 g) and the solution is stirred for seven hours at 90° C. Residue is obtained by reduced pressure condensation. By adding ethyl acetate and ether to the residue, crystallization is performed. The crystals are separated through filtration, dried and thus, 1-(4-benzyloxybenzyl)-2-methyl-6-[(2-pyridylmethyl)carbamoyl]benzimidazole (0.375 g) is obtained. 1H-NMR (DMSO-d6, δ): 2.59 (3H, s), 4.78 (2H, d, J=4.8 Hz), 5.01 (2H, s), 5.31 (2H, s), 6.89 (2H, d, J=8.7 Hz), 6.99 (2H, d, J=8.6 Hz), 7.21 (1H, dd, J=5.1 and 7.4 Hz), 7.29-7.42 (6H, m), 7.62 (1H, br t), 7.65-7.75 (3H, m), 7.98 (1H, s), 8.57 (1H, d, J=4.1 Hz).

Workup

customResidue is obtained by reduced pressure condensation
customto the residue, crystallization
customThe crystals are separated through filtration
customdried

Sources & evidence

ORD record: ord-db3650eca19443c3a8e1aad4d00eccad
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06348032B1

Reaction notes

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