Sodium Hydroxide → HCID 58728737, compound

HRID 1992105Notes

Reaction equation

HRID 1992105 reaction equation
[CH3:1][C:2]1[N:6]([CH:7]2[CH2:13][C@H:12]3[N:14]([CH2:15][CH2:16][C:17]4([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=5[CH3:41])[CH2:22][CH2:21][N:20]([C:23]([C:25]5[CH:26]=[C:27]([CH:32]=[CH:33][CH:34]=5)[C:28]([O:30]C)=[O:29])=[O:24])[CH2:19][CH2:18]4)[C@H:9]([CH2:10][CH2:11]3)[CH2:8]2)[C:5]2[CH:42]=[CH:43][CH:44]=[CH:45][C:4]=2[N:3]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[N:6]([CH:7]2[CH2:13][C@H:12]3[N:14]([CH2:15][CH2:16][C:17]4([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=5[CH3:41])[CH2:22][CH2:21][N:20]([C:23]([C:25]5[CH:26]=[C:27]([CH:32]=[CH:33][CH:34]=5)[C:28]([OH:30])=[O:29])=[O:24])[CH2:19][CH2:18]4)[C@H:9]([CH2:10][CH2:11]3)[CH2:8]2)[C:5]2[CH:42]=[CH:43][CH:44]=[CH:45][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58728400HCID 58728400, compound

Product 1

HCID 58728737HCID 58728737, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 3-{[4-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-(2-methylphenyl)piperidin-1-yl]carbonyl}benzoate (0.15 g, 0.29 mmol) in methanol (1 mL) was treated with 2N sodium hydroxide solution (1.5 mL) and let stir at rt for 4 h. The mixture was concentrated to remove methanol and acidified by adding 1N hydrochloric acid. The resulting precipitate was collected, washed with water and dried to give 3-{[4-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-(2-methylphenyl) piperidin-1-yl]carbonyl}benzoic acid as a pale pink solid (0.04 g, 31%). 1H NMR (400 MHz, CD3OD) δ 8.11 (m, 1H), 8.02 (s, 1H), 7.54 (m, 3H), 7.48 (m, 1H), 7.34 (m, 1H), 7.17-7.28 (m, 5H), 5.08 (m, 1H), 4.07 (m, 1H), 3.87 (m, 2H), 3.54 (m, 2H), 3.30 (m, 1H), 2.71 (m, 2H), 2.39-2.55 (m, 10H), 2.22-2.30 (m, 6H), 2.09 (m, 3H), 1.92 (m, 1H). HRMS C37H42N4O3 m/z 591.3335 (M+H)Cal., 591.3350 (M+H)Obs..

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove methanol
  3. additionby adding 1N hydrochloric acid
  4. customThe resulting precipitate was collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-7ee706cdb89c425db35cf47e7f5dbd27
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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