Formic Acid → HCID 20139718, compound

HRID 1252330Notes

Reaction equation

HRID 1252330 reaction equation
[CH:1]([C:4]1([CH3:18])[N:8]2[C:9](=[O:16])[C:10]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[C:7]2=[N:6][C:5]1=[O:17])([CH3:3])[CH3:2].[CH2:19]([SH:22])[CH:20]=[CH2:21].C(N(CC)CC)C.C(O)=O>O1CCCC1>[CH2:19]([S:22][C:7]12[NH:6][C:5](=[O:17])[C:4]([CH:1]([CH3:3])[CH3:2])([CH3:18])[N:8]1[C:9](=[O:16])[C:10]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=1)[CH:20]=[CH2:21]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 13367Allyl MercaptanHCID 13246864HCID 13246864, compound

Product 1

HCID 20139718HCID 20139718, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 7.8 g of 3-isopropyl-3-methyl-3H-imidazo[1',2':1,2]pyrrolo[3,4-b]pyridine-2,5-dione in 50 ml of tetrahydrofuran are stirred together with 3.5 ml of allylmercaptan and 4.9 ml of triethylamine. The mixture is stirred further for 15 hours at room temperature. In order to work up the reaction mixture, 1.2 ml of formic acid are added and most of the solvent is evaporated off. The residue is chromatographed through a column of silica gel eluted with a 1:1 mixture of ethyl acetate and hexane. The eluant is evaporated off off, leaving a residue which crystallises. Yield: 3.2 g of the title product; m.p.: 126°-138° C.

Workup

  1. additionare added and most of the solvent
  2. customis evaporated off
  3. customThe residue is chromatographed through a column of silica gel
  4. washeluted with a 1:1 mixture of ethyl acetate and hexane
  5. customThe eluant is evaporated off off,
  6. customleaving a residue which
  7. customcrystallises

Sources & evidence

ORD record
ord-617904563e8745ce842b3d604935ab84
Source dataset
uspto-grants-1988_05
Patent number
US04743296

Reaction notes

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