2-Aminothiazole → 2-(4-Cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-N-thiazol-2-yl-acetamide

HRID 524422Notes

Reaction equation

HRID 524422 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([O:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[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.[NH2:48][C:49]1[S:50][CH:51]=[CH:52][N:53]=1>C(Cl)Cl>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([O:17][CH:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[C:14]([NH:48][C:49]3[S:50][CH:51]=[CH:52][N:53]=3)=[O:15])=[CH:11][CH:12]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59610020(4-Cyclopropanesulfonyl-phenyl)-[(tetrahydro-pyran-4-yloxy)]-acetic acid

Product 1

HCID 888617632-(4-Cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-N-thiazol-2-yl-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(4-Cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-acetic acid (preparation 4; (1 equi.) and HATU (1.5 equi) was dissolved in DCM. To this solution was added D1PEA (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. additionTo this solution was added D1PEA (2 equi.)
  2. stirringto stir over night at room temperature
  3. customReaction mixture
  4. washwashed with water, brine
  5. dry with materialdried over anhydrous sodium sulfate, solvent
  6. customwas removed under reduced pressure
  7. customto get the crude compound which
  8. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-180cb57c676e41079b274b9122972185
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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