2-Aminothiazole → 6-(5-(phenylethynyl)thiophene-2-yl)-N-(2,4,4-trimethylpentane-2-yl)imidazo[2,1-b]thiazole-5-amine

HRID 1366234

Reaktionsgleichung

Reaktionsgleichung von HRID 1366234
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[C:7]1([C:13]#[C:14][C:15]2[S:19][C:18]([CH:20]=O)=[CH:17][CH:16]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:22][C:23]([N+:30]#[C-:31])([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH3:24].Cl(O)(=O)(=O)=O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:7]1([C:13]#[C:14][C:15]2[S:19][C:18]([C:20]3[N:1]=[C:2]4[N:6]([C:31]=3[NH:30][C:23]([CH3:24])([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH3:22])[CH:5]=[CH:4][S:3]4)=[CH:17][CH:16]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

7

Edukt 5

HCID 21552-AminothiazoleHCID 10340Sodium CarbonateHCID 24247Perchloric AcidHCID 267251,1,3,3-Tetramethylbutyl isocyanideHCID 27371405-(Phenylethynyl)thiophene-2-carbaldehyde

Produkt 1

HCID 248759586-(5-(phenylethynyl)thiophene-2-yl)-N-(2,4,4-trimethylpentane-2-yl)imidazo[2,1-b]thiazole-5-amineAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 400 mg (4.0 mmol) 2-aminothiazole, 1018 mg (4.8 mmol) 5-phenylethynyl-thiophene-2-carbaldehyde, 557 mg (4.0 mmol) (2,4,4-trimethylpentane-2-yl)-isocyanide and 400 μl of a 20% aq. perchloric acid was stirred in DCM (8 ml) for 5 d at RT. A 1 molar aq. Na2CO3 sol. was subsequently added. The phases were separated and the aqueous phase was extracted with DCM. The collected organic phases were washed with brine and dried over MgSO4. After filtering and removal of the solvent in a vacuum, a CC (AE/hexane 1:4) was performed with the residue, whereby 637 mg (1.47 mmol, 37%) 6-(5-(phenylethynyl)thiophene-2-yl)-N-(2,4,4-trimethylpentane-2-yl)imidazo[2,1-b]thiazole-5-amine was obtained.

Aufarbeitung

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with DCM
  3. washThe collected organic phases were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtering
  6. customremoval of the solvent in a vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a2845a41776046949978bb693ed40b77
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893069B2

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