Hydrochloric Acid → 1-{[1-(3-Pyrrolidin-1-ylbenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzimidazol-2-yl]methyl}cyclopentanecarboxylic acid

HRID 1776780Notes

Reaction equation

[N:1]1([C:6]2[CH:7]=[C:8]([CH:41]=[CH:42][CH:43]=2)[CH2:9][N:10]2[C:14]3[CH:15]=[CH:16][C:17]([O:19][CH2:20][C:21]4[CH:30]=[CH:29][C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[N:22]=4)=[CH:18][C:13]=3[N:12]=[C:11]2[CH2:31][C:32]2([C:37]([O:39]C)=[O:38])[CH2:36][CH2:35][CH2:34][CH2:33]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1COCC1.[Li+].[OH-].Cl>C(Cl)Cl.O.CO>[N:1]1([C:6]2[CH:7]=[C:8]([CH:41]=[CH:42][CH:43]=2)[CH2:9][N:10]2[C:14]3[CH:15]=[CH:16][C:17]([O:19][CH2:20][C:21]4[CH:30]=[CH:29][C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[N:22]=4)=[CH:18][C:13]=3[N:12]=[C:11]2[CH2:31][C:32]2([C:37]([OH:39])=[O:38])[CH2:36][CH2:35][CH2:34][CH2:33]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a 20 mL vial were added methyl 1-((1-(3-(pyrrolidin-1-yl)benzyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)cyclopentanecarboxylate (20.7 mg, 0.04 mmol), THF (1 mL) and MeOH (1 mL) followed by treatment with LiOH (1 mL, 1 M). The reaction mixture was capped and heated to 80° C. for 3 h. The mixture was cooled to RT, water (5 mL) was added and the pH was adjusted to ˜4 using 1 M HCl. To the mixture was added DCM (5 mL) and the mixture was stirred for 1 h at RT. The organic layer was separated then concentrated to dryness. The resulting residue was purified using FCC to provide the title compound. MS (ESI): mass calcd. for C35H36N4O3, 560.28; m/z found, 561.1 [M+H]+.

Workup

customThe reaction mixture was capped
temperatureThe mixture was cooled to RT
customThe organic layer was separated
concentrationthen concentrated to dryness
customThe resulting residue was purified

Sources & evidence

ORD record: ord-2c6145530a9d42c9947f88028a83931c
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265770B2

Reaction notes

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