Diisopropyl Ether → HCID 22754726, compound

HRID 66335Notes

Reaction equation

HRID 66335 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[N:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14]([N:18]3[CH:26]([O:27]C(OC4C=CC=CC=4)=O)[C:25]4[C:20](=[N:21][CH:22]=[CH:23][N:24]=4)[C:19]3=[O:37])=[N:15]2)=[CH:10][CH:9]=1.[CH:38]([O:41]C(C)C)(C)C>CN(C)C=O>[Cl:7][C:8]1[N:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14]([N:18]3[CH:26]([O:27][C:38]([N:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)=[O:41])[C:25]4[C:20](=[N:21][CH:22]=[CH:23][N:24]=4)[C:19]3=[O:37])=[N:15]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 8082PiperidineHCID 233436456-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-5-phenoxycarbonyloxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine

Product 1

HCID 22754726HCID 22754726, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of piperidine (3.06 g.) in anhydrous dimethylformamide (5 cc.) is added to a suspension of 6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-5-phenoxycarbonyloxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine (5.2 g.) in anhydrous dimethylformamide (21 cc.). The reaction mixture is stirred for 15 minutes at a temperature of about 25° C., after which diisopropyl ether (75 cc.) is added. The insoluble product is filtered off, washed with diisopropyl ether (4 × 10 cc.) and then treated with methylene chloride (100 cc.). A slight amount of insoluble matter is filtered off, and the organic solution obtained is then washed by twice successively decanting it with 1N sodium hydroxide solution (25 cc.) and water (25 cc.), dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. After recrystallising the residue obtained from acetonitrile (130 cc.), 6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-5-piperidinocarbonyloxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine (2.25 g.), melting at 249° C., is obtained.

Workup

  1. filtrationThe insoluble product is filtered off
  2. washwashed with diisopropyl ether (4 × 10 cc.)
  3. additiontreated with methylene chloride (100 cc.)
  4. filtrationA slight amount of insoluble matter is filtered off
  5. customthe organic solution obtained
  6. washis then washed
  7. customby twice successively decanting it with 1N sodium hydroxide solution (25 cc.) and water (25 cc.)
  8. dry with materialdried over anhydrous sodium sulphate
  9. customevaporated to dryness under reduced pressure
  10. customAfter recrystallising the residue

Sources & evidence

ORD record
ord-ff75daa5220746d6a5be1b38af68712b
Source dataset
uspto-grants-1978_12
Patent number
US04131674

Reaction notes

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