Water → HCID 178508970, compound

HRID 1296805Notes

Reaction equation

HRID 1296805 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=O)=[CH:2]1.COC1C=CC(/C=[C:27]2/[C:28]([NH:30][C:31]([S:33]/2)=[NH:32])=[O:29])=CC=1OC1CCCC1.C([O-])(=O)C.[Na+].O>C(O)(=O)C>[NH2:32][C:31]1[S:33]/[C:27](=[CH:10]\[C:3]2[C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[NH:1][CH:2]=2)/[C:28](=[O:29])[N:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 517045Sodium AcetateHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 137629131(5Z)-5-[(3-cyclopentyloxy-4-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one

Product 1

HCID 178508970HCID 178508970, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The suspension of 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (example 1b, 200 mg, 1.4 mmol), pseudothiohydantoin (159 mg, 1.4 mmol), and sodium acetate (459 mg, 5.6 mmol) in acetic acid (2 mL) was stirred under reflux for 12 h. After cooling to room temperature, water was added. The solid was collected by filtration, washed with water and dried to obtain 2-amino-5-[1-(1H-pyrrolo[2,3-b]pyridin-3-yl)-meth-(Z)-ylidene]-thiazol-4-one (280 mg, 82%) as a slight yellow solid. LC-MS m/e 245 (MH+).

Workup

  1. temperatureunder reflux for 12 h
  2. filtrationThe solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-8933953e4a4646c7b6a978d023ae779c
Source dataset
uspto-grants-2007_07
Patent number
US07247727B2

Reaction notes

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