2-Aminothiazole → HCID 86687570, compound

HRID 1473515Notes

Reaction equation

HRID 1473515 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[Cl:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([S:19](OC3C(F)=C(F)C(F)=C(F)C=3F)(=[O:21])=[O:20])=[C:15]([F:18])[CH:16]=2)[N:11]=[CH:10][CH:9]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1.[Cl-].[NH4+]>[Cl:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([S:19]([NH:1][C:2]3[S:3][CH:4]=[CH:5][N:6]=3)(=[O:21])=[O:20])=[C:15]([F:18])[CH:16]=2)[N:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 21552-AminothiazoleHCID 2733832Lithium HexamethyldisilazideHCID 86687568HCID 86687568, compound

Product 1

HCID 86687570HCID 86687570, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
-78 °C

Procedure

A flask containing a solution of 2-aminothiazole (0.039 g, 0.386 mmol) and perfluorophenyl 4-chloro-6-fluoroquinoline-7-sulfonate (0.150 g, 0.351 mmol) in THF (1.754 ml) was cooled to −78° C. for 10 minutes, and then lithium bis(trimethylsilyl)amide, 1.0 m solution in tetrahydrofuran (0.701 ml, 0.701 mmol) was added drop wise (conversion from colorless solution to yellow-orange). After 20 minutes, the reaction was diluted with sat. aq ammonium chloride solution, and was extracted with DCM:MeOH (90:10) (×3). The organics were dried over sodium sulfate, filtered and concentrated in vacuo. The material was taken forward crude. m/z (ESI) 344.0 (M+H)+.

Workup

  1. extractionwas extracted with DCM:MeOH (90:10) (×3)
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-960a33a11c604ee5b18a25d0fb5b3102
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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