Pyridine → HCID 54398765, compound

HRID 1380081Notes

Reaction equation

HRID 1380081 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:22])[N:7]3[CH2:14][CH2:13][C:12](=[CH:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:8]3=[N:9][C:10]=2[CH:11]=1.[C:23]([CH2:27][CH2:28][C:29](Cl)=[O:30])([O:25][CH3:26])=[O:24].N1C=CC=CC=1>CC(N(C)C)=O>[CH3:26][O:25][C:23](=[O:24])[CH2:27][CH2:28][C:29]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:22])[N:7]3[CH2:14][CH2:13][C:12](=[CH:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:8]3=[N:9][C:10]=2[CH:11]=1)=[O:30]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 54343992HCID 54343992, compound

Product 1

HCID 54398765HCID 54398765, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

6-amino-3-benzylidene-1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazoline-9-one (2.5 g) was reacted with 3-carbometoxy propionyl chloride (1.95 g) in dimethylacetamide (110 ml) in the presence of pyridine (2 ml) at room temperature for 18 hours. The reaction mixture was then diluted with ice water and the precipitate was filtered and washed with water to give 3-[N-(3-benzylidene-9-oxo-1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazolin-6-yl)-aminocarbonyl]-propanoic acid methyl ester, m.p. 288°-291° C. (3.3 g) which was dissolved in dimethylformamide (120 ml) and treated with 5% aqueous NaOH (32.5 ml) at room temperature for 3 hours. The precipitate, 3-[N-(3-benzylidene-9-oxo-1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazolin-6-yl)-aminocarbonyl]-propanoic acid, sodium salt, m.p. >300° C., was filtered and washed with water, then it was dissolved in formic acid and the solution was diluted with water to give a precipitate which was filtered and washed with water until neutral to give 2.07 g of 3-[N-(3-benzylidene-9-oxo-1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazolin-6-yl)-aminocarbonyl]-propanoic acid, m.p. 250°-255° C. dec., NMR (DMSO d6) δ ppm., 2.62 (bs) (4H, --COCH2CH2 --COOH), 3.18 (m) (2H, C-2 protons), 4.08 (t) (2H, C-1 protons), 7.30-7.70 (m) (7H, C-5 and C-7 protons and phenyl protons), 7.98 (d) (1H, C-8 proton), 8.07 (t) (1H, --CH=), 10.31 (ds) (1H, --NHCO--).

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-71d5f1df376043f3b23832dab41db43e
Source dataset
uspto-grants-1986_04
Patent number
US04579847

Reaction notes

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