3-Hydroxypiperidine → HCID 86623159, compound

HRID 1948447Notes

Reaction equation

HRID 1948447 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[CH:12]=[C:13]([S:17](Cl)(=[O:19])=[O:18])[S:14][C:15]=2[Br:16])=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].[OH:21][CH:22]1[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Br:16][C:15]1[S:14][C:13]([S:17]([N:24]2[CH2:25][CH2:26][CH2:27][CH:22]([OH:21])[CH2:23]2)(=[O:19])=[O:18])=[CH:12][C:11]=1[C:7]1[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=1[CH3:10]

Participants

5

Reactant 3

HCID 232933-HydroxypiperidineHCID 81531DiisopropylethylamineHCID 866231464-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]-5-bromothiophene-2-sulfonylchloride

Product 1

HCID 86623159HCID 86623159, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]-5-bromothiophene-2-sulfonylchloride, prepared as in Step III of Example 23 (136 mg; 0.33 mmol; 1 eq), is dissolved in DCM (10 ml). 3-hydroxy piperidine (0.20 ml; 1.65 mmol; 5 eq) and DIEA (0.17 ml; 0.98 mmol; 3 eq) are added under a nitrogen atmosphere. After 2 hours reaction, solvents are evaporated. The crude product is dissolved in DCM and washed with NH4Cl saturated solution, water and dried over MgSO4. After evaporation of the solvents, crude material is purified by reverse preparative HPLC, affording N-(5-{2-bromo-5-[(3-hydroxypiperidin-1-yl)sulfonyl]-3-thienyl}-4-methyl-1,3-thiazol-2-yl)acetamide as an oil (31 mg; 20%).

Workup

  1. customAfter 2 hours reaction, solvents
  2. customare evaporated
  3. dissolutionThe crude product is dissolved in DCM
  4. washwashed with NH4Cl saturated solution, water
  5. dry with materialdried over MgSO4
  6. customAfter evaporation of the solvents, crude material
  7. customis purified by reverse preparative HPLC

Sources & evidence

ORD record
ord-2b86b4381ac84e5085d3c70ad1b31e87
Source dataset
uspto-grants-2013_03
Patent number
US08399497B2

Reaction notes

Loading…