3-Nitro-6-chloro-N-(thiazolo[4,5-c]pyridin-2-ylmethyl)pyridin-2-amine → 6-Chloro-N2-(thiazolo[4,5-c]pyridin-2-ylmethyl)pyridine-2,3-diamine

HRID 876841Notes

Reaction equation

HRID 876841 reaction equation
[N+:1]([C:4]1[C:5]([NH:11][CH2:12][C:13]2[S:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][C:16]=3[N:21]=2)=[N:6][C:7]([Cl:10])=[CH:8][CH:9]=1)([O-])=O>CO.C1COCC1.[Pd]>[Cl:10][C:7]1[N:6]=[C:5]([NH:11][CH2:12][C:13]2[S:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][C:16]=3[N:21]=2)[C:4]([NH2:1])=[CH:9][CH:8]=1

Participants

5

Reactant 1

HCID 866714403-Nitro-6-chloro-N-(thiazolo[4,5-c]pyridin-2-ylmethyl)pyridin-2-amine

Product 1

HCID 866714416-Chloro-N2-(thiazolo[4,5-c]pyridin-2-ylmethyl)pyridine-2,3-diamine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10% Pd/C (20 mg) was added to a solution of 3-nitro-6-chloro-N-(thiazolo[4,5-c]pyridin-2-ylmethyl)pyridin-2-amine (100 mg, 0.31 mmol) in MeOH (2 mL) and THF (10 mL). The mixture was stirred at room temperature under 1 atm of H2 for 1 h, and then filtered. The filtrate was concentrated and purified by chromatography on silica gel to afford the title compound. MS (m/z): 292 (M+1)+.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-1376f74e7311459f92ee76c877de6343
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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