Hydrochloric Acid → HCID 18382046, compound

HRID 2297509Notes

Reaction equation

HRID 2297509 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([CH2:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[N:17])[CH:14]=3)[NH:9][CH:8]=2)[CH2:2]1.[Cl:18][CH2:19][CH2:20][N:21]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][C:22]1=[O:32].C(=O)([O-])O.[Na+].Cl>CN(C)C=O.C(O)C>[ClH:18].[O:32]=[C:22]1[N:21]([CH2:20][CH2:19][N:1]2[CH2:5][CH2:4][CH:3]([CH2:6][C:7]3[C:15]4[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[N:17])[CH:14]=4)[NH:9][CH:8]=3)[CH2:2]2)[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 787663-(2-chloroethyl)(1H,3H)quinazoline-2,4-dioneHCID 516892Sodium BicarbonateHCID 15511271HCID 15511271, compound

Product 1

HCID 18382046HCID 18382046, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

Under an inert atmosphere and at ambient temperature, 47.3 mmol (10 g) of 3-[3-pyrrolidinylmethyl]-1H-indole-5-carbonitrile, 47.3 mmol (9.97 g) of 3-(2-chloroethyl)-2,4-(1H,3H)-quinazolinedione and 47.3 mmol (3.73 g) of sodium hydrogen carbonate are dissolved in 100 ml of dimethylformamide, and stirring is carried out at 100° C. for 6 hours. The reaction mixture is concentrated and the residue is taken up in dichloromethane. The organic phase is washed with water and then with saturated sodium chloride solution, and is dried over magnesium sulphate. Purification is carried out by chromatography on silica using a mixture of dichloromethane/methanol/ammonia 95/5/0.5 as eluant. The compound obtained is converted into the salt by one equivalent of hydrochloric acid in ethanol.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. washThe organic phase is washed with water
  3. dry with materialwith saturated sodium chloride solution, and is dried over magnesium sulphate
  4. customPurification
  5. additiona mixture of dichloromethane/methanol/ammonia 95/5/0.5 as eluant
  6. customThe compound obtained

Sources & evidence

ORD record
ord-68f232220a474dfbb53e227b7dfaab5d
Source dataset
uspto-grants-2002_12
Patent number
US06492366B1

Reaction notes

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