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

HRID 1366236Notes

Reaction equation

HRID 1366236 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.N1C=CC=C[C:8]=1C#CC1SC(C=O)=CC=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)Cl.C(Cl)Cl>[CH3:22][C:23]([NH:30][C:31]1[N:6]2[C:2]([S:3][CH:4]=[CH:5]2)=[N:1][CH:8]=1)([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH3:24]

Participants

8

Reactant 5

HCID 21552-AminothiazoleHCID 10340Sodium CarbonateHCID 24247Perchloric AcidHCID 267251,1,3,3-Tetramethylbutyl isocyanideHCID 862301905-Pyridin-2-ylethynyl-thiophene-2-carbaldehyde

Product 1

HCID 131728708N-(2,4,4-trimethylpentane-2-yl)imidazo[2,1-b]thiazole-5-amine

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5.0 g (50.0 mmol) 2-amino-thiazole, 10.7 g (50.0 mmol) 5-(pyridine-2-yl-ethynyl)-thiophene-2-carbaldehyde, 7.0 g (50.0 mmol) (2,4,4-trimethylpentane-2-yl)-isocyanide and 1.0 ml of a 70% aq. perchloric acid in chloroform (25 ml) was heated to 50° C. while being stirred for 5 d. 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. 11.86 g (27.3 mmol, 55%) 6-(5-pyridine-2-ylethynyl)thiophene-2-yl)-N-(2,4,4-trimethylpentane-2-yl)imidazo[2,1-b]thiazole-5-amine was obtained by multiple crystallisation of the residue from AE.

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-d1e8e57cc9214cd59a55f5fd75d599fc
Source dataset
uspto-grants-2011_02
Patent number
US07893069B2

Reaction notes

Loading…