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Piperazine → N-sec-butyl-5-(4-(2-fluorophenyl)-1H-imidazol-5-yl)thiazolo[5,4-b]pyridin-2-amine

HRID 1452981
Notes
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Reaction equation

HRID 1452981 reaction equation
[CH:1]([NH:5][C:6]1[S:7][C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[C:10]([CH:15]=O)[N:9]=2)([CH2:3][CH3:4])[CH3:2].[NH4+].[OH-].[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]([N+:37]#[C-:38])S(C1C=CC(C)=CC=1)(=O)=O.[NH:39]1CCNCC1>C1COCC1.CCOC(C)=O>[CH:1]([NH:5][C:6]1[S:7][C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[C:10]([C:15]1[NH:39][CH:38]=[N:37][C:26]=1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[F:19])[N:9]=2)([CH2:3][CH3:4])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 4837PiperazineHCID 14923Ammonium HydroxideHCID 467382311-Fluoro-2-(isocyano(tosyl)methyl)benzeneHCID 575272422-(Sec-butylamino)thiazolo[5,4-b]pyridine-5-carbaldehyde

Product 1

HCID 15986167N-sec-butyl-5-(4-(2-fluorophenyl)-1H-imidazol-5-yl)thiazolo[5,4-b]pyridin-2-amineYield 26%

Reagents, catalysts & solvents

2
HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(sec-butylamino)thiazolo[5,4-b]pyridine-5-carbaldehyde (presumed 0.24 mmol, 1.0 eq.) and concentrated aqueous NH4OH (0.050 mL) in THF (0.8 mL) was stirred overnight. 1-Fluoro-2-(isocyano(tosyl)methyl)benzene (0.0841 g, 0.291 mmol, 1.2 eq.) and piperazine (0.0394 g, 0.457 mmol, 1.9 eq.) were added, and the reaction mixture was stirred overnight. It was then diluted with EtOAc and washed with water, saturated aqueous NaHCO3, and brine, dried over Na2SO4, filtered, and concentrated in vacuo. MeOH was added to the residue, and the mixture was subjected to autoprep. The appropriate fractions were collected, and NaHCO3 (s) was added. The solution was then concentrated in vacuo not to dryness and extracted with CH2Cl2 (3×). The organic layers were combined, dried over Na2SO4, filtered, and concentrated in vacuo to give N-sec-butyl-5-(4-(2-fluorophenyl)-1H-imidazol-5-yl)thiazolo[5,4-b]pyridin-2-amine as a yellow solid (0.0228 g, 26% yield). LC/MS (MH)=368.23.

Workup

  1. washwashed with water, saturated aqueous NaHCO3, and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. additionMeOH was added to the residue
  6. customThe appropriate fractions were collected
  7. additionNaHCO3 (s) was added
  8. concentrationThe solution was then concentrated in vacuo not to dryness
  9. extractionextracted with CH2Cl2 (3×)
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fcaeeb2d481f490c886903533dd9eb1f
Source dataset
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07473784B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes