Triethylamine → HCID 86723567, compound

HRID 2170914Notes

Reaction equation

HRID 2170914 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C:7]([OH:9])=O)[S:5][CH:6]=1.Cl.[F:11][C:12]([F:17])([F:16])[C@@H:13]([NH2:15])[CH3:14].CCN(CC)CC>O=S(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[N:3]=[C:4]([C:7]([NH:15][C@@H:13]([CH3:14])[C:12]([F:17])([F:16])[F:11])=[O:9])[S:5][CH:6]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 130939192-Propanamine, 1,1,1-trifluoro-, hydrochloride (1:1), (2S)-HCID 151220654-Bromo-1,3-thiazole-2-carboxylic acid

Product 1

HCID 86723567HCID 86723567, compoundYield 53.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 24386Thionyl ChlorideSolvent

Procedure

To the mixture of 4-bromothiazole-2-carboxylic acid (80 g, 1.0 eq.) in SOCl2 (300 ml) was added DMF (10 drops). It was refluxed for 5 hours and concentrated. The residue was dissolved in DCM (300 ml) and added to the solution of (S)-1,1,1-trifluoropropan-2-amine hydrochloride (60.5 g, 1.05 eq.) with Et3N (117 g, 3.0 eq.) at 0° C. It was stirred overnight. TLC and LCMS showed the reaction was complete. It was quenched with water and extracted with DCM. The organic phase was dried, filtered and concentrated. The residue was purified by column to obtain 62 g (53% y) of (S)-4-bromo-N-(1,1,1-trifluoropropan-2-yl)thiazole-2-carboxamide.

Workup

  1. temperatureIt was refluxed for 5 hours
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in DCM (300 ml)
  4. customIt was quenched with water
  5. extractionextracted with DCM
  6. customThe organic phase was dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column

Sources & evidence

ORD record
ord-81a6b89547274877b5007b7adb483c56
Source dataset
uspto-grants-2015_06
Patent number
US09051313B2

Reaction notes

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