Hydrochloric Acid → HCID 10127140, compound

HRID 457726Notes

Reaction equation

HRID 457726 reaction equation
[OH:1][C@H:2]1[C@H:11]([O:12][CH2:13][CH2:14][O:15][CH3:16])[C:10]2[CH:9]=[CH:8][N:7]3[C:17]([CH3:21])=[C:18]([CH3:20])[N:19]=[C:6]3[C:5]=2[NH:4][C@@H:3]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[H-].[Na+].[CH3:30][O:31][C:32](Cl)=[O:33].Cl>O1CCCC1>[CH3:30][O:31][C:32]([O:1][C@H:2]1[C@H:11]([O:12][CH2:13][CH2:14][O:15][CH3:16])[C:10]2[CH:9]=[CH:8][N:7]3[C:17]([CH3:21])=[C:18]([CH3:20])[N:19]=[C:6]3[C:5]=2[NH:4][C@@H:3]1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 24758Sodium hydrideHCID 213054Soraprazan

Product 1

HCID 10127140HCID 10127140, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 2 g of (7R,8R,9R)-8-hydroxy-7-(2-methoxyethoxy)-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine in 30 ml of dry tetrahydrofuran is treated in small portions with 0.34 g of sodium hydride suspension (80% strength in paraffin) and stirred at room temperature for 30 minutes, then 0.66 g of methylchloroformate is added dropwise and the mixture is stirred for 3 h. It is then poured onto ice water, neutralized with semiconcentrated aqueous hydrochloric acid and extracted three times with a little ethyl acetate, and the collected organic phases are washed with a little water and dried over potassium carbonate. The volatile components are stripped off in vacuo and the solid residue is purified on silica gel (eluent: diethyl ether). 1.2 g of the title compound of melting point 176–77° C. (diethyl ether) are obtained.

Workup

  1. stirringthe mixture is stirred for 3 h
  2. additionIt is then poured onto ice water
  3. extractionextracted three times with a little ethyl acetate
  4. washthe collected organic phases are washed with a little water
  5. dry with materialdried over potassium carbonate
  6. customthe solid residue is purified on silica gel (eluent: diethyl ether)

Sources & evidence

ORD record
ord-a6b2540b3ed44036917bf16f5ac79294
Source dataset
uspto-grants-2007_03
Patent number
US07189736B2

Reaction notes

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