Triethylamine → HCID 86702357, compound

HRID 1422565Notes

Reaction equation

HRID 1422565 reaction equation
N[C:2]1[N:7]=[C:6](/[CH:8]=[C:9]2/[C:10](=[O:15])[NH:11][C:12](=[O:14])[S:13]/2)[CH:5]=[CH:4][N:3]=1.[O:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:21](Cl)=[O:22].C([N:26](CC)CC)C.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[O:14]=[C:12]1[NH:11][C:10](=[O:15])[C:9](=[CH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:19]3[CH:18]=[C:17]([C:21]([NH2:26])=[O:22])[O:16][CH:20]=3)[N:7]=2)[S:13]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 516892Sodium BicarbonateHCID 86702356HCID 86702356, compound

Product 1

HCID 86702357HCID 86702357, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(Z)—N-(4-(((2,4-dioxothiazolidin-5-ylidene)methyl)pyrimidin-2-yl)furan-2-carboxamide was prepared as follows. A 2-dram vial charged with (Z)-5-((2-aminopyrimidin-4-yl)methylene)thiazolidine-2,4-dione (30.4 mg, 0.137 mmol), Pyridine (1.1 mL), furan-2-carbonyl chloride (107 mg, 0.821 mmol, 6 equiv.), triethylamine (83 mg, 0.821 mmol, 6 equiv.), and shaken at RT. After 16 h, the reaction was treated with saturated sodium bicarbonate (3 mL) and extracted with DCE (3×3 mL). The combined organic layer was concentrated under reduced pressure and the residue was purified using reverse phase HPLC to provide the desired product (14 mg, 43.3 mg theoretical, 32.4%). LC-MS m/z 317.3 (M+1).

Workup

  1. extractionextracted with DCE (3×3 mL)
  2. concentrationThe combined organic layer was concentrated under reduced pressure
  3. customthe residue was purified

Sources & evidence

ORD record
ord-17c63a124ad74d98aa85189c17fe28ed
Source dataset
uspto-grants-2015_01
Patent number
US08927525B2

Reaction notes

Loading…