2-Aminothiazole → HCID 24876135, compound

HRID 1366237Notes

Reaction equation

HRID 1366237 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]#[C:14][C:15]1[O:19][C:18]([CH:20]=O)=[CH:17][CH:16]=1.[C:22]([N+:26]#[C-:27])([CH3:25])([CH3:24])[CH3:23].Cl(O)(=O)(=O)=O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl>[C:22]([NH:26][C:27]1[N:6]2[C:2]([S:3][CH:4]=[CH:5]2)=[N:1][C:20]=1[C:18]1[O:19][C:15]([C:14]#[C:13][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][N:7]=2)=[CH:16][CH:17]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

8

Reactant 5

HCID 21552-AminothiazoleHCID 10340Sodium CarbonateHCID 23577Tert-Butyl isocyanideHCID 24247Perchloric AcidHCID 87217901HCID 87217901, compound

Product 1

HCID 24876135HCID 24876135, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 380 mg (3.8 mmol) 2-amino-thiazole, 749 mg (3.8 mmol) 5-(pyridine-2-yl-ethynyl)-furan-2-carbaldehyde, 378 mg (3.8 mmol) tert.butyl-isonitril and 73 μl of a 70% aq. perchloric acid in chloroform (2 ml) was heated to 45° C. while being stirred for 16 h. Dilution with DCM was subsequently performed and a 1 molar aq. Na2CO3 sol. was added. After 10 min of stirring at RT, the phases were separated. The aqueous phase was extracted with DCM. The collected organic phases were dried over Na2SO4, filtered and concentrated in a vacuum. 472 mg (1.3 mmol, 34%) N-tert-butyl-6-(5-(pyridine-2-ylethynyl)furan-2-yl)imidazo[2,1-b]thiazole-5-amine was obtained by CC (AE) with the residue.

Workup

  1. stirringAfter 10 min of stirring at RT
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with DCM
  4. dry with materialThe collected organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-44ffb026b87549be8c5962a9ad703445
Source dataset
uspto-grants-2011_02
Patent number
US07893069B2

Reaction notes

Loading…