2-Aminothiazole → HCID 10408333, compound

HRID 729717Notes

Reaction equation

HRID 729717 reaction equation
CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([CH:32]([CH2:36][CH:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)[C:33]([OH:35])=O)=[CH:28][CH:27]=1)(=[O:25])=[O:24].[S:43]1[CH:47]=[CH:46][N:45]=[C:44]1[NH2:48]>CN(C=O)C>[CH3:22][S:23]([C:26]1[CH:27]=[CH:28][C:29]([CH:32]([CH2:36][CH:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)[C:33]([NH:48][C:44]2[S:43][CH:47]=[CH:46][N:45]=2)=[O:35])=[CH:30][CH:31]=1)(=[O:24])=[O:25]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 210940042-[4-(Methanesulfonyl)phenyl]-3-(oxan-4-yl)propanoic acid

Product 1

HCID 10408333HCID 10408333, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

EDCI (80 mg, 420 μmol) and HOBt (56 mg, 420 μmol) were added to a stirred solution of 2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)propionic acid (Preparation 41, 100 mg, 320 μmol) in anhydrous DMF (6 mL). After 15 min, the solution was treated with thiazol-2-ylamine (38 mg, 380 μmol). The mixture was stirred at 20° C. for 16 h, before being concentrated under reduced pressure. The residue was partitioned between CH2Cl2 and saturated aqueous Na2CO3. The organic layer was washed with 1M HCl and dried (MgSO4). Filtration and solvent evaporation yielded the title compound: RTA=3.16 min; m/z (ES+)=436.2 [M+MeCN+H]+.

Workup

  1. concentrationbefore being concentrated under reduced pressure
  2. customThe residue was partitioned between CH2Cl2 and saturated aqueous Na2CO3
  3. washThe organic layer was washed with 1M HCl
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and solvent evaporation

Sources & evidence

ORD record
ord-ca4bf1956a894026946187e81139327d
Source dataset
uspto-grants-2009_09
Patent number
US07582632B2

Reaction notes

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