Hydrochloric Acid → HCID 68447707, compound

HRID 2104441Notes

Reaction equation

HRID 2104441 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][C@@H:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[NH:20][C:21]([C:23]1[S:24][C:25]3[CH2:26][NH:27][CH2:28][CH2:29][C:30]=3[N:31]=1)=[O:22])=[O:13])=[CH:6]2.C(O[BH-](O[C:42](=O)[CH3:43])OC(=O)C)(=O)C.[Na+].[OH-].[Na+].Cl.[CH2:49](Cl)Cl>C(O)C.CC(C)=O.C(O)(=O)C.C(N(CC)CC)C>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][C@@H:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[NH:20][C:21]([C:23]1[S:24][C:25]3[CH2:26][N:27]([CH:42]([CH3:43])[CH3:49])[CH2:28][CH2:29][C:30]=3[N:31]=1)=[O:22])=[O:13])=[CH:6]2

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 6344Dichloromethane2×HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 68451909N-((1R*,2R)-2-{[(5-Chloroindol-2-yl)carbonyl]amino}-cyclopentyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamide hydrochloride

Product 1

HCID 68447707HCID 68447707, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

The compound (30 mg) obtained in Example 23 was suspended in methylene chloride (20 mL), and triethylamine (260 μl) was added, followed by stirring at room temperature for 15 minutes. Acetic acid (179 μl) and acetone (920 μl) were added to the reaction mixture, and the resultant mixture was stirred at room temperature for 2 minutes. Sodium triacetoxyborohydride (796 mg) was added to the reaction mixture to stir them at room temperature for 5 hours. 1N aqueous sodium hydroxide (10 mL) was added to the reaction mixture for partitioning the mixture. The resultant organic layer was dried over sodium sulfate anhydrate, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride:methanol=100:3) to give a colorless foamy substance. This product was dissolved in methylene chloride, and 1N HCl in ethanol (1 mL) was added. The solution was concentrated under reduced pressure to give the title compound (205 mg).

Workup

  1. stirringto stir them at room temperature for 5 hours
  2. customfor partitioning the mixture
  3. dry with materialThe resultant organic layer was dried over sodium sulfate anhydrate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (methylene chloride:methanol=100:3)
  6. customto give a colorless foamy substance
  7. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9ee78d318ce34de28fa42fc2c2cd8091
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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