Water → HCID 68787251, compound

HRID 1376276Notes

Reaction equation

HRID 1376276 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:26])[N:7]([S:13]([C:16]3[CH:17]=[C:18]([NH2:25])[C:19](=[CH:23][CH:24]=3)[C:20]([OH:22])=[O:21])(=[O:15])=[O:14])[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[C:27](Cl)(=[O:30])[CH2:28][CH3:29].O>O1CCOCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:26])[N:7]([S:13]([C:16]3[CH:17]=[C:18]([NH:25][C:27](=[O:30])[CH2:28][CH3:29])[C:19](=[CH:23][CH:24]=3)[C:20]([O:22][C:5]([CH3:10])([CH3:6])[CH3:4])=[O:21])(=[O:15])=[O:14])[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 62324Propionyl chlorideHCID 9802095HCID 9802095, compound

Product 1

HCID 68787251HCID 68787251, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

840 mg (1.86 mmol) of Compound 17 was dissolved in 8 ml of 1,4-dioxane, 240 μl (2.79 mmol) of propionyl chloride was added dropwise, then the resultant mixture was stirred overnight at 60° C. An excess of water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer thus obtained was washed, dried, and concentrated to obtain a crude product of t-butyl 4-[(7-chloro-2,4(1H,3H)-quinazolinedion-3-yl)sulfonyl]-2-N-propionylanthranilate. The obtained crude product was stirred at room temperature in 3 ml of trifluoroacetic acid for 1 hour, then the reaction solution was concentrated in vacuo to obtain a crude product. This was washed by diethyl ether to obtain 400 mg (yield 48%: 2-steps) of the above-identified compound. Properties: colorless crystal, Melting point: >200° C. (decomposition), PMR (δ ppm, DMSO-d6): 1.10 (3H, t), 2.45 (2H, dd), 7.11 (1H, s), 7.24 (1H, d), 7.85 (1H, d), 7.88 (1H, d), 8.17 (1H, d), 9.18 (1H, s), 11.07 (1H, s), 11.63 (1H, s).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer thus obtained
  3. washwas washed
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-865c0f38325e43fdb7287819df47102f
Source dataset
uspto-grants-2007_01
Patent number
US07169951B2

Reaction notes

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