Hydrochloric Acid → 2-{1-[4-(5,5-Dimethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-thiazol-2-yl]piperidin-4-ylamino}ethanol

HRID 1401837Notes

Reaction equation

HRID 1401837 reaction equation
Cl.[CH3:2][C:3]1([CH3:25])[CH2:12][CH2:11][CH2:10][C:9]2[CH:8]=[C:7]([C:13]3[N:14]=[C:15]([N:18]4[CH2:23][CH2:22][CH:21]([NH2:24])[CH2:20][CH2:19]4)[S:16][CH:17]=3)[CH:6]=[CH:5][C:4]1=2.[Si]([O:33][CH2:34][CH:35]=O)(C(C)(C)C)(C)C.Cl>O1CCOCC1>[CH3:2][C:3]1([CH3:25])[CH2:12][CH2:11][CH2:10][C:9]2[CH:8]=[C:7]([C:13]3[N:14]=[C:15]([N:18]4[CH2:23][CH2:22][CH:21]([NH:24][CH2:35][CH2:34][OH:33])[CH2:20][CH2:19]4)[S:16][CH:17]=3)[CH:6]=[CH:5][C:4]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 683807081-[4-(5,5-Dimethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamine hydrochloride

Product 1

HCID 673233642-{1-[4-(5,5-Dimethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-thiazol-2-yl]piperidin-4-ylamino}ethanol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The preparation is carried out as described starting from 60 mg (0.16 mmol) of 1-[4-(5,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamine hydrochloride and 34 μl (0.16 mmol) of (tert-butyldimethylsilanyloxy)acetaldehyde. The protecting group is cleaved off using a 4N HCl solution in dioxane. The purification is carried out by means of preparative HPLC. The product is in the form of the formate.

Workup

  1. customThe purification

Sources & evidence

ORD record
ord-b87204c1c7774a9180dea2431445911b
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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