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

HRID 1948403Notes

Reaction equation

HRID 1948403 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-5ff18b59190b4a628c8574aa98bc5589
Source dataset
uspto-grants-2013_03
Patent number
US08399497B2

Reaction notes

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