Dimethylformamide → HCID 86621993, compound

HRID 1715264Notes

Reaction equation

HRID 1715264 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[N:12]=[C:13]([C:16]([OH:18])=O)[S:14][CH:15]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].C(Cl)(=O)C([Cl:22])=O.CN(C)C=O>C(Cl)Cl>[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[N:12]=[C:13]([C:16]([Cl:22])=[O:18])[S:14][CH:15]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 11989523HCID 11989523, compound2×

Product 1

HCID 86621993HCID 86621993, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2′-(Acetylamino)-4′-methyl-4,5′-bi-1,3-thiazole-2-carboxylic acid, Compound (4), (100 mg; 0.35 mmol; 1 eq.) is suspended in DCM (6 ml). Oxalyl chloride (92 μl; 1.06 mmol; 3 eq.) is added followed by anhydrous dimethylformamide (5.5 μl; 0.07 mmol; 0.20 eq.). After 2 hours, a sample is quenched with MeOH, showing that the reaction is complete. The solvents are evaporated affording 2′-acetylamino-4′-methyl-[4,5′]bithiazolyl-2-carbonyl chloride which is used in the next step without further purification. HPLC (method A), Rt: 1.90 min (purity: 92.0%).

Workup

  1. customa sample is quenched with MeOH
  2. customThe solvents are evaporated

Sources & evidence

ORD record
ord-a1281def5631494ebd40e4559e732046
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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