Acetic Acid → HCID 178457042, compound

HRID 1364486Notes

Reaction equation

HRID 1364486 reaction equation
S([O-])([O-])(=O)=O.[Mg+2].[CH:7]([C:9]1[S:13][C:12]([C:14]2[S:18][C:17]([NH:19][C:20](=[O:22])[CH3:21])=[N:16][C:15]=2[CH3:23])=[CH:11][CH:10]=1)=O.[CH2:24]([NH2:27])[CH:25]=[CH2:26].C(O)(=O)C>C1COCC1>[CH2:24](/[N:27]=[CH:7]/[C:9]1[S:13][C:12]([C:14]2[S:18][C:17]([NH:19][C:20](=[O:22])[CH3:21])=[N:16][C:15]=2[CH3:23])=[CH:11][CH:10]=1)[CH:25]=[CH2:26]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7853AllylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 11993393Acetamide, N-[5-(5-formyl-2-thienyl)-4-methyl-2-thiazolyl]-2×

Product 1

HCID 178457042HCID 178457042, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Anhydrous magnesium sulfate (94 mg; 0.78 mmol; 4.15 eq.) and N-[5-(5-formyl-2-thienyl)-4-methyl-1,3-thiazol-2-yl]acetamide, Compound (1), (50 mg; 0.19 mmol; 1 eq.), are added to a solution of allylamine (17 μl ; 0.23 mmol; 1.20 eq.) and acetic acid (16 μl; 0.28 mmol; 1.50 eq.) in dry THF (5 ml). The reaction is stirred at rt overnight. The mixture is filtered and rinsed with anhydrous THF and DCM, affording N-(5-{5-[(E)-(allylimino)methyl]-2-thienyl}-4-methyl-1,3-thiazol-2-yl)acetamide which is used in the next step without further purification (57.3 mg, quantitative).

Workup

  1. filtrationThe mixture is filtered
  2. washrinsed with anhydrous THF and DCM

Sources & evidence

ORD record
ord-3c568ed4de264019a92f86246e2886ef
Source dataset
uspto-grants-2011_02
Patent number
US07888379B2

Reaction notes

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