Acetic Anhydride → HCID 90411145, compound

HRID 717350Notes

Reaction equation

HRID 717350 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:13]=[C:12]([C:14]([OH:16])=[O:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>O1CCCC1>[C:17]([NH:1][CH2:2][CH2:3][C:4]1[N:13]=[C:12]([C:14]([OH:16])=[O:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 90411044HCID 90411044, compound

Product 1

HCID 90411145HCID 90411145, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 500-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 2-(2-aminoethyl)quinazoline-4-carboxylic acid (3.2 g, 14.73 mmol, 1.00 equiv) in tetrahydrofuran (32 mL). This was followed by the addition of acetyl acetate (32 mL) dropwise with stirring at room temperature. The resulting solution was stirred for 18 h at room temperature. The reaction was then quenched by the addition of 50 mL of water. The mixture was concentrated under vacuum. The crude product was purified by Flash. This resulted in 900 mg (24%) of 2-(2-acetamidoethyl)quinazoline-4-carboxylic acid as a white solid. MS (ESI) m/z 260 ([M+H]+).

Workup

  1. customInto a 500-mL 4-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringThe resulting solution was stirred for 18 h at room temperature
  4. customThe reaction was then quenched by the addition of 50 mL of water
  5. concentrationThe mixture was concentrated under vacuum
  6. customThe crude product was purified by Flash
  7. customThis resulted in 900 mg (24%) of 2-(2-acetamidoethyl)quinazoline-4-carboxylic acid as a white solid

Sources & evidence

ORD record
ord-affd4a98c0714ab7aea3fd80b225a4b2
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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