Hydrochloric Acid → HCID 58318231, compound

HRID 447165Notes

Reaction equation

HRID 447165 reaction equation
[OH:1][CH2:2][C:3]1[CH:34]=[CH:33][C:6]2[N:7]=[C:8]([N:10]3[CH2:15][CH2:14][N:13]([C:16](=[O:32])[C@@H:17]([NH:24]C(=O)OC(C)(C)C)[CH2:18][C:19]4[S:20][CH:21]=[CH:22][CH:23]=4)[CH2:12][CH2:11]3)[S:9][C:5]=2[CH:4]=1.Cl>O1CCOCC1>[NH2:24][C@@H:17]([CH2:18][C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)[C:16]([N:13]1[CH2:12][CH2:11][N:10]([C:8]2[S:9][C:5]3[CH:4]=[C:3]([CH2:2][OH:1])[CH:34]=[CH:33][C:6]=3[N:7]=2)[CH2:15][CH2:14]1)=[O:32]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67237616HCID 67237616, compound

Product 1

HCID 58318231HCID 58318231, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The (S)-tert-butyl 1-(4-(6-(hydroxymethyl)benzo[d]thiazol-2-yl)piperazin-1-yl)-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate (83 mg) was dissolved in dry 1,4-dioxane (3 mL) and HCl (4N in 1,4-dioxane, 1 mL) was added. The resulting solution was stirred overnight at room temperature, then concentrated to a white solid. The solid was chromatographed (94.5:5:0.5 dichloromethane:methanol:ammonium hydroxide) to yield the title compound as a colorless oil, which was added to HCl/ether to yield (S)-2-amino-1-(4-(6-(hydroxymethyl)benzo[d]thiazol-2-yl)piperazin-1-yl)-3-(thiophen-2-yl)propan-1-one as a white precipitate, which was collected by filtration.

Workup

  1. concentrationconcentrated to a white solid
  2. customThe solid was chromatographed (94.5:5:0.5 dichloromethane:methanol:ammonium hydroxide)

Sources & evidence

ORD record
ord-8fe488974c9e4916ac914a7e9c7320ba
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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