Water → Tert-butyl 4-((2-(2-aminophenyl)thiazolo[5,4-b]pyridin-6-yl)methyl)piperazine-1-carboxylate

HRID 2265042Notes

Reaction equation

HRID 2265042 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][C:15]([CH2:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1)=[CH:14][N:13]=2)([O-])=O.[NH4+].[Cl-].O>[Fe].CO>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][C:15]([CH2:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1)=[CH:14][N:13]=2

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 59679924Tert-butyl 4-((2-(2-nitrophenyl)thiazolo[5,4-b]pyridin-6-yl)methyl)piperazine-1-carboxylate

Product 1

HCID 59679847Tert-butyl 4-((2-(2-aminophenyl)thiazolo[5,4-b]pyridin-6-yl)methyl)piperazine-1-carboxylateYield 81.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 4-((2-(2-nitrophenyl)thiazolo[5,4-b]pyridin-6-yl)methyl)piperazine-1-carboxylate (2.13 g, 4.7 mmol), NH4Cl (2.00 g, 37 mmol), iron powder (1.31 g, 23.5 mmol), H2O (40 mL) and methanol (160 mL) was refluxed for 3 h under N2. The reaction mixture was filtered, and the filtrate was concentrated in vacuo and purified by silica gel chromatography (petroleum ether: ethyl acetate: Et3N=800:200:1) to afford tert-butyl 4-((2-(2-aminophenyl)thiazolo[5,4-b]pyridin-6-yl)methyl)piperazine-1-carboxylate as a yellow solid (1.63 g, yield: 81%).

Workup

  1. temperaturewas refluxed for 3 h under N2
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. custompurified by silica gel chromatography (petroleum ether: ethyl acetate: Et3N=800:200:1)

Sources & evidence

ORD record
ord-8a3859fa6fe34322959a3d3165273d63
Source dataset
uspto-grants-2010_12
Patent number
US07855289B2

Reaction notes

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