N-(2-aminoethyl)acetamide → HCID 11998433, compound

HRID 1360865Notes

Reaction equation

HRID 1360865 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].[C:20]([NH:23][CH2:24][CH2:25][NH2:26])(=[O:22])[CH3:21].CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[C:20]([NH:23][CH2:24][CH2:25][NH:26][S:16]([C:14]1[S:15][C:11]([C:7]2[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=2[CH3:10])=[CH:12][CH:13]=1)(=[O:18])=[O:17])(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 66082N-(2-aminoethyl)acetamideHCID 81531DiisopropylethylamineHCID 866225625-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride

Product 1

HCID 11998433HCID 11998433, compound

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

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 a mixture of DCM/DMF(1/1, 10 ml). N-acetylethylene diamine (168 mg; 1.65 mmol; 5 eq) and DIEA (0.17 ml; 0.98 mmol; 3 eq) are added. After 3 hours, 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) and title compound precipitates with diethyl ether, affording after filtration, Compound (13) as a yellow powder (14 mg; 11%).

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 diethyl ether
  8. customaffording
  9. filtrationafter filtration, Compound (13) as a yellow powder (14 mg; 11%)

Sources & evidence

ORD record
ord-110d32668a4a488793b98e9816e2a7f4
Source dataset
uspto-grants-2011_02
Patent number
US07879888B2

Reaction notes

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