Hydrochloric Acid → HCID 59543038, compound

HRID 1876336Notes

Reaction equation

HRID 1876336 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:12][CH2:13][C@@H:14]2[CH2:18][S:17][C:16]([C:19]3[NH:20][C:21]4[C:26]([CH:27]=3)=[CH:25][C:24]([Cl:28])=[CH:23][C:22]=4[NH:29][CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[N:15]2)[CH:8]=[N:9][C:10]=1[CH3:11])=[O:5])C.CO.O.[OH-].[Li+].Cl>O1CCCC1.O>[Cl:28][C:24]1[CH:25]=[C:26]2[C:21](=[C:22]([NH:29][CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[CH:23]=1)[NH:20][C:19]([C:16]1[S:17][CH2:18][C@@H:14]([CH2:13][CH2:12][N:7]3[C:6]([C:4]([OH:5])=[O:3])=[C:10]([CH3:11])[N:9]=[CH:8]3)[N:15]=1)=[CH:27]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 595430933-{2-[(R)-2-(5-chloro-7-cyclopentylamino-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]-ethyl}-5-methyl-3H-imidazole-4-carboxylic acid ethyl ester

Product 1

HCID 59543038HCID 59543038, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound (35 mg, 0.07 mmol) prepared in Example 109 was dissolved in tetrahydrofuran (10 ml), methanol (10 ml) and water (10 ml). Lithium hydroxide monohydrate (29 mg, 0.70 mmol) was added thereto, and the mixture was stirred for 8 h at room temperature. After completion of the reaction, 1N hydrochloric acid solution was added. The mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure, and purified by column chromatography to give the title compound (17 mg, Yield 52%).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationThe filtrate was distilled under reduced pressure
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-5d4d5070f74f42dc9f1fe19296108621
Source dataset
uspto-grants-2012_11
Patent number
US08309586B2

Reaction notes

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