13519-16-9 → HCID 178492303, compound

HRID 2093060Notes

Reaction equation

HRID 2093060 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]#[N:11])=[CH:5][CH:4]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][C:20]([C:22]1[S:23][C:24]2[CH2:25][NH:26][CH2:27][CH2:28][C:29]=2[N:30]=1)=[O:21]>ClC1C=CC=CC=1>[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][C:20]([C:22]1[S:23][C:24]2[CH2:25][N:26]([C:10](=[NH:11])[NH:9][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[CH2:27][CH2:28][C:29]=2[N:30]=1)=[O:21]

Participants

4

Reactant 2

HCID 1093158813519-16-9HCID 58117006N-(2-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide

Product 1

HCID 178492303HCID 178492303, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of 4-methoxy-phenyl-cyanamide (2 eq) obtained in step I above and N-(2-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide obtained in step VIII of example I (1.0 eq) in chlorobenzene was refluxed for 6 h. Solvent was evaporated and the residue was treated with ethereal HCl at room temperature for 5-15 h. Solvent was evaporated and the residue was dissolved in methanol—DCM system and neutralized. Organic layer was separated, dried on anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product, which was then purified, by either column chromatography or preparative HPLC to afford the title compound.

Workup

  1. customSolvent was evaporated
  2. additionthe residue was treated with ethereal HCl at room temperature for 5-15 h
  3. customSolvent was evaporated
  4. dissolutionthe residue was dissolved in methanol—DCM system
  5. customOrganic layer was separated
  6. dry with materialdried on anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto afford crude product, which
  9. customwas then purified, by either column chromatography or preparative HPLC

Sources & evidence

ORD record
ord-599c697f744a4866bc7cfc6c3ee056ac
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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