Piperidin-4-ol → N-(5-[5-[(4-hydroxypiperidin-1-yl)sulfonyl]-2-thienyl]-4-methyl-1,3-thiazol-2-yl)acetamide

HRID 1364490Notes

Reaction equation

HRID 1364490 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[S:15][C:14]([S:16](Cl)(=[O:18])=[O:17])=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].[OH:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[OH:20][CH:21]1[CH2:26][CH2:25][N:24]([S:16]([C:14]2[S:15][C:11]([C:7]3[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=3[CH3:10])=[CH:12][CH:13]=2)(=[O:18])=[O:17])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 79341Piperidin-4-olHCID 81531DiisopropylethylamineHCID 866225625-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride

Product 1

HCID 11993493N-(5-[5-[(4-hydroxypiperidin-1-yl)sulfonyl]-2-thienyl]-4-methyl-1,3-thiazol-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-[2-(acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride, prepared as in Step 1 of Example 9 (110 mg; 0.33 mmol; 1 eq.), is dissolved in DCM (10 ml). 4-Hydroxypiperidine (66.1 mg; 0.65 mmol; 2 eq.) and DIEA (0.17 ml; 0.98 mmol; 3 eq.) are added. After one hour, the 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, Compound (10) is obtained as white-off solid (33 mg; 23%). 1H NMR (DMSO-d6) δ 1.40-1.60 (m, 2H), 1.72-1.85 (m, 2H), 2.14 (s, 3H), 2.42 (s, 3H), 2.80-2.92 (m, 2H), 3.15-3.30 (m, 2H), 3.59 (m, 1H), 4.71 (d, J=3 Hz, 1H), 7.30 (d, J=4.5 Hz, 1H), 7.58 (d, J=4.5 Hz, 1H), 12.18 (br s, 1H). M−(ESI): 400.20; M+(ESI): 402.10. HPLC, Rt: 2.86 min (purity: 100%).

Workup

  1. customthe solvents are evaporated
  2. dissolutionThe crude product is dissolved in DCM
  3. washwashed with NH4Cl saturated solution, water
  4. dry with materialdried over MgSO4
  5. customAfter evaporation of the solvents

Sources & evidence

ORD record
ord-1e603a9489024de187921b04eb9ea0e7
Source dataset
uspto-grants-2011_02
Patent number
US07888379B2

Reaction notes

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