Dimethylformamide → HCID 86652445, compound

HRID 1948428Notes

Reaction equation

HRID 1948428 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.Cl.[NH2:29][C@H:30]1[CH2:35][CH2:34][C@H:33]([OH:36])[CH2:32][CH2:31]1.CN(C=O)C>C(Cl)Cl>[Br:16][C:15]1[S:14][C:13]([S:17](=[O:19])(=[O:18])[NH:29][CH:30]2[CH2:35][CH2:34][CH:33]([OH:36])[CH2:32][CH2:31]2)=[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

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 866231464-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]-5-bromothiophene-2-sulfonylchlorideHCID 178479278HCID 178479278, compound

Product 1

HCID 86652445HCID 86652445, compoundYield 21%

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 is put under nitrogen. Triethylamine (0.7 ml; 5.05 mmol; 7 eq) and trans-4-aminocyclohexanol hydrochloride (547.1 mg; 3.61 mmol; 5 eq) are added successively. DMF (0.2 ml) is added to dissolve the amine and the reaction mixture is stirred overnight at room temperature. The reaction mixture is then washed with water, NH4Cl sat., brine and dried over MgSO4, affording the title compound (120 mg; 21%).

Workup

  1. washThe reaction mixture is then washed with water, NH4Cl sat., brine
  2. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-afc6f4863d4947a49f17aed070f6f8fc
Source dataset
uspto-grants-2013_03
Patent number
US08399497B2

Reaction notes

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