Hydrochloric Acid → HCID 68447707, compound

HRID 546506Notes

Reaction equation

HRID 546506 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.Cl[CH2:50]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])[CH3:50])[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

(±)-trans-N1-[(5-Chloroindol-2-yl)carbonyl]-N2-[(4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]-1,2-cyclopentanediamine hydrochloride (30 mg) was suspended in dichloromethane (20 ml), and triethylamine (260 μl) was added to stir the mixture 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. A 1N aqueous solution (10 ml) of sodium hydroxide was added to the reaction mixture to conduct liquid separation. The resultant organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=100:3) to obtain a colorless foamy substance. This product was dissolved in dichloromethane, and a 1N ethanol solution (1 ml) of hydrochloric acid was added. The solution was concentrated under reduced pressure to obtain the title compound (205 mg) as a pale yellow foamy substance.

Workup

  1. stirringto stir them at room temperature for 5 hours
  2. customliquid separation
  3. dry with materialThe resultant organic layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=100:3)
  6. customto obtain a colorless foamy substance
  7. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fc7a5d83051e48a798b61138a23755cf
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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