Hydrochloric Acid → HCID 86282744, compound

HRID 1776741Notes

Reaction equation

HRID 1776741 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:38]=[CH:39][CH:40]=1)[CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=3)=[CH:14][C:9]=2[N:8]=[C:7]1[CH2:27][C:28]1([C:33]([O:35]CC)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1.C1COCC1.[Li+].[OH-].Cl>C(Cl)Cl.O.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:38]=[CH:39][CH:40]=1)[CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=3)=[CH:14][C:9]=2[N:8]=[C:7]1[CH2:27][C:28]1([C:33]([OH:35])=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 90414705HCID 90414705, compound

Product 1

HCID 86282744HCID 86282744, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a 20 mL vial were added ethyl 1-{[1-(3-bromobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzimidazol-2-yl]methyl}cyclopentanecarboxylate (57 mg, 0.09 mmol), THF (1 mL) and MeOH (1 mL) followed by LiOH (1 mL, 1 M). The reaction mixture was capped and heated to 80° C. for 3 h. The mixture was then cooled to RT, water (5 mL) was added to the mixture and the pH was adjusted to ˜4 using 1 M HCl. To this mixture was added DCM (5 mL) and stirred for 1 h at RT. The organic layer was separated and the aqueous layer was further extracted with DCM. The combined organics were dried, filtered and concentrated to dryness. The residue was then purified by FCC to provide the title compound. MS (ESI): mass calcd. for C31H28BrN3O3, 569.13; m/z found, 570.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.20 (d, J=8.6, 1H), 8.11 (d, J=8.3, 1H), 7.83 (d, J=8.3, 1H), 7.77-7.72 (m, 1H), 7.69 (d, J=8.6, 1H) 7.58-7.53 (m, 1H), 7.45 (d, J=7.8, 1H), 7.36-7.34 (m, 1H), 7.23 (s, 1H), 7.21-7.15 (m, 2H), 7.11-7.06 (m, 1H), 6.90 (d, J=7.6, 1H), 5.44 (s, 2H), 5.28 (s, 2H), 3.04 (s, 2H), 2.44-2.34 (m, 2H), 1.77-1.66 (m, 2H), 1.50-1.41 (m, 4H)

Workup

  1. customThe reaction mixture was capped
  2. temperatureThe mixture was then cooled to RT
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was further extracted with DCM
  5. customThe combined organics were dried
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was then purified by FCC

Sources & evidence

ORD record
ord-cb050dd5cbd048649d40db3c451ed084
Source dataset
uspto-grants-2016_02
Patent number
US09265770B2

Reaction notes

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