Hydrochloric Acid → HCID 69156281, compound

HRID 899643Notes

Reaction equation

HRID 899643 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][CH2:15][N:16]([CH2:27][C:28]1[N:32](S(O)(=O)=O)[C:31]2[CH2:37][CH2:38][CH2:39][CH2:40][C:30]=2[N:29]=1)[CH:17]1[C:26]2[N:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:20][CH2:19][CH2:18]1.Cl.[OH-].[Na+]>>[NH:29]1[C:30]2[CH2:40][CH2:39][CH2:38][CH2:37][C:31]=2[N:32]=[C:28]1[CH2:27][N:16]([CH:17]1[C:26]2[N:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:20][CH2:19][CH2:18]1)[CH2:15][CH2:14][CH2:13][CH2:12][N:3]1[C:2](=[O:1])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]1=[O:11]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69178365HCID 69178365, compound

Product 1

HCID 69156281HCID 69156281, compoundYield 66.2%

Procedure

2-{[[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-4,5,6,7-tetrahydro-benzoimidazole-1-sulfonic acid (0.4564 g, 0.77 mmol) and 2 N HCl (7.5 mL) were stirred at reflux for 23 hours. The reaction mixture was cooled to room temperature and 15% (w/v) aqueous NaOH (5 mL) was added. The aqueous layer was extracted with CH2Cl2 (3×150 mL), and the combined organic extracts were washed with brine (1×100 mL), dried (Na2SO4), and concentrated. 0.2466 g (64%) of the crude 2-{4-[(4,5,6,7-tetrahydro-1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-butyl}-isoindole-1,3-dione was isolated as a pale yellow foam. 1H NMR (CDCl3) δ 1.37-1.39 (m, 2H), 1.79-1.88 (m, 10H), 1.98-2.11 (m, 2H), 2.51-2.63 (m, 8H), 3.50-3.52 (m, 1H), 3.66-3.86 (m, 2H), 3.97-3.99 (m, 1H), 7.02-7.11 (m, 2H), 7.37-7.40 (m, 2H), 7.68-7.71 (m, 1H), 7.80-7.82 (m, 1H), 8.44-8.46 (m, 1H).

Workup

  1. temperatureat reflux for 23 hours
  2. extractionThe aqueous layer was extracted with CH2Cl2 (3×150 mL)
  3. washthe combined organic extracts were washed with brine (1×100 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6634b708267945fc8b1aab4535949d59
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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