Ether hydrochloride → HCID 53252100, compound

HRID 447168Notes

Reaction equation

HRID 447168 reaction equation
[CH:1]1([NH:6][CH2:7][C:8]2[CH:39]=[CH:38][C:11]3[N:12]=[C:13]([N:15]4[CH2:20][CH2:19][N:18]([C:21](=[O:37])[C@@H:22]([NH:29]C(=O)OC(C)(C)C)[CH2:23][C:24]5[S:25][CH:26]=[CH:27][CH:28]=5)[CH2:17][CH2:16]4)[S:14][C:10]=3[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C(OCC)C>O1CCOCC1.Cl>[NH2:29][C@@H:22]([CH2:23][C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)[C:21]([N:18]1[CH2:19][CH2:20][N:15]([C:13]2[S:14][C:10]3[CH:9]=[C:8]([CH2:7][NH:6][CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH:39]=[CH:38][C:11]=3[N:12]=2)[CH2:16][CH2:17]1)=[O:37]

Participants

5

Reactant 2

HCID 10953452Ether hydrochlorideHCID 67236358HCID 67236358, compound

Product 1

HCID 53252100HCID 53252100, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

(S)-tert-Butyl 1-(4-(6-((cyclopentylamino)methyl)benzo[d]thiazol-2-yl)piperazin-1-yl)-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate (20 mg) was dissolved in dry 1,4-dioxane (2 ml) and HCl (4N in 1,4-dioxane). 5 mL) was added. The resulting mixture was stirred overnight at room temperature, then concentrated and chromatographed (94.5:5:0.5 dichloromethane:methanol:ammonium hydroxide) to yield a colorless oil, which was added to HCl/diethyl ether. The resulting white precipitate was collected and dried to yield the title compound.

Workup

  1. addition5 mL) was added
  2. concentrationconcentrated
  3. customchromatographed (94.5:5:0.5 dichloromethane:methanol:ammonium hydroxide)
  4. customto yield a colorless oil, which
  5. customThe resulting white precipitate was collected
  6. customdried

Sources & evidence

ORD record
ord-35da26a328c9413a896894489a8f0e0a
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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