2-Aminothiazole → 2-(4-Cyclopropanesulfonylphenyl)-2-(2,4-difluoro-phenoxy)-N-thiazol-2-yl-acetamide

HRID 1889192Notes

Reaction equation

HRID 1889192 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([O:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])[C:14](O)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:59][C:60]1[S:61][CH:62]=[CH:63][N:64]=1>C(Cl)Cl>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([O:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])[C:14]([NH:59][C:60]3[S:61][CH:62]=[CH:63][N:64]=3)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 596100322-(4-Cyclopropylsulfonylphenyl)-2-(2,4-difluorophenoxy)acetic acid

Product 1

HCID 252619862-(4-Cyclopropanesulfonylphenyl)-2-(2,4-difluoro-phenoxy)-N-thiazol-2-yl-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Procedure-C: 2-(4-cyclopropanesulfonylphenyl)-2-(2,4-difluorophenoxy)acetic acid (1 equi) (obtained in step III) and HATU (1.5 equi) was dissolved in DCM. To this solution was added DIPEA (2 equi.) and stirred for 15 minutes followed by addition of 2-aminothiazole (1 equi.) and continued to stir over night at room temperature. Reaction mixture was diluted with dichloromethane, washed with water, brine, dried over anhydrous sodium sulfate, solvent was removed under reduced pressure to get the crude compound which was purified by flash chromatography to get the title product.

Workup

  1. stirringto stir over night at room temperature
  2. customReaction mixture
  3. washwashed with water, brine
  4. dry with materialdried over anhydrous sodium sulfate, solvent
  5. customwas removed under reduced pressure
  6. customto get the crude compound which
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-1838805a072c416a955d4a4f68b3bf52
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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