2-Aminothiazole → HCID 9884180, compound

HRID 855540Notes

Reaction equation

HRID 855540 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:9]([OH:11])=O)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.[S:57]1[CH:61]=[CH:60][N:59]=[C:58]1[NH2:62]>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:9]([NH:62][C:58]2[S:57][CH:61]=[CH:60][N:59]=2)=[O:11])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 21552-AminothiazoleHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 58935724HCID 58935724, compound

Product 1

HCID 9884180HCID 9884180, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(6-chloropyridin-3-yl)-3-cyclopentylpropionic acid (Preparation 1, 0.56 g, 2.2 mmol), TBTU (1.41 g, 4.4 mmol), HOBt (0.45 g, 3.3 mmol), NEt3 (0.31 mL, 2.2 mmol), and thiazol-2-ylamine (0.44 g, 4.4 mmol) in anhydrous DMF (23 mL) was stirred at 20° C. for 16 h. The reaction mixture was diluted with EtOAc, before being washed with 2 M Na2CO3, H2O, and brine. After drying (Na2SO4), the organic phase was filtered and concentrated to give the title compound: RTA=3.82 min; m/z (ES+)=336.1 [M+H]+.

Workup

  1. washbefore being washed with 2 M Na2CO3, H2O, and brine
  2. dry with materialAfter drying (Na2SO4)
  3. filtrationthe organic phase was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-72dd1121d9974154b57c15d612dafa51
Source dataset
uspto-grants-2007_08
Patent number
US07262196B2

Reaction notes

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