Hydrochloric Acid → HCID 178478749, compound

HRID 982650Notes

Reaction equation

HRID 982650 reaction equation
C(OC(=O)[NH:7][C@@H:8]([C:19]1[NH:20][CH:21]=[C:22]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[N:23]=1)[CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)(C)(C)C.[ClH:31]>C(O)(=O)C>[ClH:31].[ClH:31].[NH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([CH2:9][C@@H:8]([NH2:7])[C:19]2[NH:20][CH:21]=[C:22]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[N:23]=2)=[CH:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178454164HCID 178454164, compound

Product 1

HCID 178478749HCID 178478749, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

[(R)-2-(1H-indol-3-yl)-1-(4-pyridin-4-yl-1H-imidazol-2-yl)-ethyl]-carbamic acid tert-butyl ester (3.46 g, 8.58 mmol) is dissolved in a mixture of glacial acetic acid (99.5%, 25 ml) and conc. aq. HCl (37%, 2.5 ml) and the solution is stirred under argon at room temperature for 1 h. The resulting precipitate is filtered, washed with acetone and dried to give 3.04 g (94%) of (R)-2-(1H-indol-3-yl)-1-(4-pyridin-4-yl-1H-imidazol-2-yl)-ethylamine dihydrochloride (TLC: silica gel, toluene:ethanol:AcOH 4:4:1, Rf=0.18).

Workup

  1. filtrationThe resulting precipitate is filtered
  2. washwashed with acetone
  3. customdried

Sources & evidence

ORD record
ord-c46bde6c27204b1bbad8d5c734c54969
Source dataset
uspto-grants-2005_03
Patent number
US06861430B2

Reaction notes

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