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Diisopropylethylamine → N-[5-(5-[[(2,2-Dimethyl-1,3-dioxolan-4-YL)methyl]aminosulfonyl}-2-thienyl)-4-methyl-1,3-thiazol-2-YL]acetamide

HRID 1948404
Notes
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Reaction equation

HRID 1948404 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].[CH3:20][C:21]1([CH3:28])[O:25][CH:24]([CH2:26][NH2:27])[CH2:23][O:22]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:20][C:21]1([CH3:28])[O:25][CH:24]([CH2:26][NH:27][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][O:22]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 41223491,3-Dioxolane-4-methanamine, 2,2-dimethyl-HCID 866225625-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride

Product 1

HCID 11998434N-[5-(5-[[(2,2-Dimethyl-1,3-dioxolan-4-YL)methyl]aminosulfonyl}-2-thienyl)-4-methyl-1,3-thiazol-2-YL]acetamide

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

5-[2-(acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride, prepared as in Step II of Example 1 (110 mg; 0.33 mmol; 1 eq), is dissolved in DCM (10 ml). 2.2-Dimethyl-1,3-dioxolane-4-methanamine (216 mg; 1.65 mmol; 5 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, crude material is dissolved in DCM (3 ml). Title compound precipitates with addition diethyl ether, affording after filtration, Compound (14) as a white powder (65 mg; 46%).

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, crude material
  6. dissolutionis dissolved in DCM (3 ml)
  7. customTitle compound precipitates with addition diethyl ether
  8. customaffording
  9. filtrationafter filtration, Compound (14) as a white powder (65 mg; 46%)

Sources & evidence

ORD record
ord-03f86cd7a3af47b9b48d6ebe9d83378b
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08399497B2

Reaction notes

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