Triethylamine → (1-[4-(2-Acetylamino-4-methyl-thiazol-5-yl)-5-bromo-thiophene-2-sulfonyl]-piperidin-4-yl}-methyl-carbamic acid tert-butyl ester

HRID 1948425Notes

Reaction equation

HRID 1948425 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].C(N(CC)CC)C.[C:28]([O:32][C:33](=[O:42])[N:34]([CH3:41])[CH:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)([CH3:31])([CH3:30])[CH3:29]>C(Cl)Cl>[C:28]([O:32][C:33](=[O:42])[N:34]([CH:35]1[CH2:36][CH2:37][N:38]([S:17]([C:13]2[S:14][C:15]([Br:16])=[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]=2)(=[O:19])=[O:18])[CH2:39][CH2:40]1)[CH3:41])([CH3:31])([CH3:29])[CH3:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27568064-N-Boc-4-N-Methyl-aminopiperidineHCID 866231464-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]-5-bromothiophene-2-sulfonylchloride

Product 1

HCID 86652444(1-[4-(2-Acetylamino-4-methyl-thiazol-5-yl)-5-bromo-thiophene-2-sulfonyl]-piperidin-4-yl}-methyl-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[2-(acetylamino)-4-methyl-1,3-thiazol-5-yl]-5-bromothiophene-2-sulfonyl chloride, prepared as in Step III of Example 23 (300 mg; 0.72 mmol; 1 eq), is dissolved in anhydrous DCM (20 ml). The reaction mixture is put under nitrogen. Triethylamine (0.5 ml; 3.61 mmol; 5 eq) and methyl-piperidine-4-yl-carbamic acid tert-butyl ester (773.2 mg; 3.61 mmol; 5 eq) are added successively and the reaction mixture is stirred for 30 minutes at room temperature. It is then washed with water, NaHCO3 sat., brine and dried over MgSO4, affording the title compound (470 mg; quantitative).

Workup

  1. washIt is then washed with water, NaHCO3 sat., brine
  2. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-33b8decf2ebb47ceae338063d2e8230a
Source dataset
uspto-grants-2013_03
Patent number
US08399497B2

Reaction notes

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