Diisopropyl Ether → HCID 21438294, compound

HRID 2397447Notes

Reaction equation

HRID 2397447 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)[CH:2]=[CH2:3].[Cl:10][C:11]1[N:20]=[C:19]2[C:14]([CH:15]=[CH:16][C:17]([N:21]3[CH:25]([O:26][C:27](OC4C=CC=CC=4)=[O:28])[C:24]4[S:36][CH2:37][CH2:38][O:39][C:23]=4[C:22]3=[O:40])=[N:18]2)=[CH:13][CH:12]=1.C(OC(C)C)(C)C>C(#N)C>[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([C:27]([O:26][CH:25]2[N:21]([C:17]3[CH:16]=[CH:15][C:14]4[C:19](=[N:20][C:11]([Cl:10])=[CH:12][CH:13]=4)[N:18]=3)[C:22](=[O:40])[C:23]3[O:39][CH2:38][CH2:37][S:36][C:24]2=3)=[O:28])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 8064221-AllylpiperazineHCID 23343641HCID 23343641, compound

Product 1

HCID 21438294HCID 21438294, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Allylpiperazine (6.3 g.) is added to a suspension of 6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-5-phenoxycarbonyloxy-2,3,6,7-tetrahydro-5H-1,4-oxathiino[2,3-c]pyrrole (4.56 g.) in acetonitrile (25 cc.). The temperature of the reaction mixture rises to about 25° C. After 29 hours, diisopropyl ether (50 cc.) is added and the insoluble product is filtered off and washed with diisopropyl ether (2 × 15 cc.). After drying, 5-(4-allylpiperazine-1-yl)carbonyloxy-6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-2,3,6,7-tetrahydro-5H-1,4-oxathiino[2,3-c]pyrrole (3.1 g.), melting at 254° C., is obtained.

Workup

  1. customrises to about 25° C
  2. filtrationthe insoluble product is filtered off
  3. washwashed with diisopropyl ether (2 × 15 cc.)
  4. customAfter drying

Sources & evidence

ORD record
ord-9c4dccda4fee483987999a1c20983237
Source dataset
uspto-grants-1977_05
Patent number
US04021554

Reaction notes

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