Lithium hydroxide, monohydrate → HCID 59833449, compound

HRID 269748Notes

Reaction equation

HRID 269748 reaction equation
C([O:3][C:4](=[O:46])[CH2:5][CH2:6][CH2:7][N:8]([C:38]1[CH:43]=[C:42]([CH3:44])[CH:41]=[C:40]([CH3:45])[CH:39]=1)[CH2:9][C:10]1[CH:37]=[CH:36][C:13]2[N:14]=[C:15]([NH:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[N:16]([CH2:17][C:18]3[C:23]([OH:24])=[CH:22][CH:21]=[C:20]([CH3:25])[N:19]=3)[C:12]=2[CH:11]=1)C.[Li+].[OH-].O>O1CCCC1.O>[CH3:44][C:42]1[CH:43]=[C:38]([N:8]([CH2:9][C:10]2[CH:37]=[CH:36][C:13]3[N:14]=[C:15]([NH:26][CH2:27][CH2:28][CH2:29][N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)[N:16]([CH2:17][C:18]4[C:23]([OH:24])=[CH:22][CH:21]=[C:20]([CH3:25])[N:19]=4)[C:12]=3[CH:11]=2)[CH2:7][CH2:6][CH2:5][C:4]([OH:46])=[O:3])[CH:39]=[C:40]([CH3:45])[CH:41]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59833498HCID 59833498, compound2×

Product 1

HCID 59833449HCID 59833449, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-{(3,5-dimethyl-phenyl)-[3-(3-hydroxy-6-methyl-pyridin-2-ylmethyl)-2-(3-morpholin-4-yl-propylamino)-3H-benzoimidazol-5-ylmethyl]-amino}-butyric acid ethyl ester (Compound 71), prepared as described for compounds n-4, (0.000175 mol) and LiOH/H2O (0.00035 mol) in tetrahydrofuran (8 ml) and H2O (8 ml) was stirred at room temperature for 12 hours. The tetrahydrofuran was evaporated and a 1N solution of NaOH in water was added. The solution was extracted with CH2Cl2/CH3OH (95/5). The organic layer was separated, dried (over MgSO4), filtered and the solvent was evaporated. The residue was taken up in H2O. The precipitate was filtered off and dried, yielding 0.059 g of 4-{(3,5-dimethyl-phenyl)-[3-(3-hydroxy-6-methyl-pyridin-2-ylmethyl)-2-(3-morpholin-4-yl-propylamino)-3H-benzoimidazol-5-ylmethyl]-amino}-butyric acid (Compound 62, 56%, melting point: 121° C.).

Workup

  1. customprepared
  2. customThe tetrahydrofuran was evaporated
  3. additiona 1N solution of NaOH in water was added
  4. extractionThe solution was extracted with CH2Cl2/CH3OH (95/5)
  5. customThe organic layer was separated
  6. dry with materialdried (over MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. filtrationThe precipitate was filtered off
  10. customdried

Sources & evidence

ORD record
ord-ad8d2b5bc3ba421a9dc92be9d3905466
Source dataset
uspto-grants-2008_11
Patent number
US07449463B2

Reaction notes

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