Hydrochloric Acid → HCID 15908472, compound

HRID 480026Notes

Reaction equation

HRID 480026 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][N:6]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[C:9](=[O:16])[NH:8][C:7]1=[O:17].[F:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.Cl>N1C=CC=CC=1>[O:17]=[C:7]1[NH:8][C:9](=[O:16])[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=2[N:6]1[CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[S:25]([C:22]1[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=1)(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 95884-Fluorobenzenesulfonyl chlorideHCID 18768328HCID 18768328, compound

Product 1

HCID 15908472HCID 15908472, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 75 mg (0.32 mmol) of 1-[3-(methylamino)propyl]-5,6,7,8-tetrahydro-2,4(1H,3H)-quinazolinedione and 61.5 mg (0.32 mmol) of 4-fluorophenylsulphonyl chloride in 3 ml of pyridine is stirred at room temperature overnight. The reaction mixture is then adjusted to pH 1 using 2-molar hydrochloric acid and extracted twice with in each case 20 ml of ethyl acetate. The organic phase is concentrated under reduced pressure and the resulting residue is purified by preparative HPLC (RP-C18, acetonitrile/water gradient). This gives 43.1 mg (34% yield) of the product as an amorphous solid.

Workup

  1. extractionextracted twice with in each case 20 ml of ethyl acetate
  2. concentrationThe organic phase is concentrated under reduced pressure
  3. customthe resulting residue is purified by preparative HPLC (RP-C18, acetonitrile/water gradient)

Sources & evidence

ORD record
ord-2d358a7a2aff40029844bc40a68edc6b
Source dataset
uspto-grants-2003_11
Patent number
US06649618B2

Reaction notes

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