Lithium Hydroxide → HCID 90415381, compound

HRID 2178486Notes

Reaction equation

HRID 2178486 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:45]=[CH:44][C:10]([CH2:11][N:12]3[C:16]4[CH:17]=[CH:18][C:19]([O:21][CH2:22][C:23]5[CH:32]=[CH:31][C:30]6[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=6)[N:24]=5)=[CH:20][C:15]=4[N:14]=[C:13]3[CH2:33][C:34]3([C:39]([O:41]CC)=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C1COCC1.[Li+].[OH-]>CO>[N:4]1([C:7]2[CH:8]=[CH:9][C:10]([CH2:11][N:12]3[C:16]4[CH:17]=[CH:18][C:19]([O:21][CH2:22][C:23]5[CH:32]=[CH:31][C:30]6[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=6)[N:24]=5)=[CH:20][C:15]=4[N:14]=[C:13]3[CH2:33][C:34]3([C:39]([OH:41])=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:44][CH:45]=2)[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 90414283HCID 90414283, compound

Product 1

HCID 90415381HCID 90415381, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a 20 mL vial were added ethyl 1-((1-(4-morpholinobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)cyclopentanecarboxylate (28 mg, 0.046 mmol), THF (1.1 mL) and MeOH (1.1 mL) followed by LiOH (0.65 mL, 1 M). The reaction mixture was capped and heated to 80° C. for 3 h. The mixture was cooled to RT and the solvent was concentrated to dryness. Water (1 mL) and acetonitrile (1 mL) were added and the pH was adjusted to ˜5-6 using 1 M HCl and then the mixture was concentrated to dryness. The resulting residue was purified using FCC to provide the title compound. MS (ESI): mass calcd. for C35H36N4O4, 576.27; m/z found, 577.2 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.20 (d, J=8.5, 1H), 8.11 (d, J=8.4, 1H), 7.83 (d, J=8.1, 1H), 7.77-7.72 (m, 1H), 7.69 (d, J=8.5, 1H), 7.58-7.53 (m, 1H), 7.33-7.31 (m, 1H), 7.22 (d, J=8.9, 1H), 7.10-7.05 (m, 1H), 6.97-6.93 (m, 2H), 6.85-6.80 (m, 2H), 5.43 (s, 2H), 5.22 (s, 2H), 3.86-3.81 (m, 4H), 3.14-3.09 (m, 4H), 3.05 (s, 2H), 2.41-2.33 (m, 2H), 1.75-1.66 (m, 2H), 1.47-1.39 (m, 4H).

Workup

  1. customThe reaction mixture was capped
  2. temperatureThe mixture was cooled to RT
  3. concentrationthe solvent was concentrated to dryness
  4. additionWater (1 mL) and acetonitrile (1 mL) were added
  5. concentrationthe mixture was concentrated to dryness
  6. customThe resulting residue was purified

Sources & evidence

ORD record
ord-809d6a3831754d8c84fd5d633a0eb156
Source dataset
uspto-grants-2015_06
Patent number
US09067917B2

Reaction notes

Loading…