Formic Acid → HCID 57634214, compound

HRID 661074Notes

Reaction equation

HRID 661074 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([NH:24][C:25](=[O:31])OC(C)(C)C)[S:5][C:6]=1[C:7](=O)[NH:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[S:15]C(=S)N(CC)CC.C(O)(C(F)(F)F)=O.C(Cl)Cl.C(N(CC)C(SC1C=NC=CC=1NC(C1SC(N)=NC=1Br)=O)=S)C.C(O)=O>C([SiH](CC)CC)C>[Br:1][C:2]1[N:3]=[C:4]([NH:24][CH:25]=[O:31])[S:5][C:6]=1[C:7]1[S:15][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:9]=2[N:8]=1

Participants

7

Reactant 5

HCID 284Formic AcidHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 57634095HCID 57634095, compoundHCID 57634172HCID 57634172, compound

Product 1

HCID 57634214HCID 57634214, compound

Reagents, catalysts & solvents 1

HCID 12052TriethylsilaneCatalyst

Procedure

To a 100 mL round-bottomed flask was added tert-butyl 4-bromo-5-((3-(diethylcarbamothioylthio)pyridin-4-yl)carbamoyl)thiazol-2-ylcarbamate (1.0 g, 1.8 mmol) and a 1:1 mixture of TFA (0.14 mL, 1.8 mmol) and DCM (0.12 mL, 1.8 mmol) with a few drops of triethylsilane. The solution was then stirred at room temperature. LCMS indicated that the reaction was complete after about 1 hour. The solvents were removed, and the resulting oil was used without further manipulation. To a 100 mL round-bottomed flask was added 4-(2-amino-4-bromothiazole-5-carboxamido)pyridin-3-yl diethylcarbamodithioate (0.82 g, 1.8 mmol) and formic acid (0.070 mL, 1.8 mmol), and the mixture was heated at 100° C. for about 2 hours. LCMS indicated no remaining starting material, so the solvent was removed and 2 N ammonia in MeOH was added. An orange precipitate formed which was filtered and determined to be the product N-(4-bromo-5-(thiazolo[5,4-c]pyridin-2-yl)thiazol-2-yl) formamide.

Workup

  1. customThe solvents were removed
  2. temperaturethe mixture was heated at 100° C. for about 2 hours
  3. customso the solvent was removed
  4. addition2 N ammonia in MeOH was added
  5. customAn orange precipitate formed which
  6. filtrationwas filtered

Sources & evidence

ORD record
ord-22eff01aee1e42e69a6f46221bc8cb1b
Source dataset
uspto-grants-2011_12
Patent number
US08084479B2

Reaction notes

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