Lithium hydroxide, monohydrate → (1,3)Thiazolo(4,5-c)pyridin-2-amine

HRID 2190319Notes

Reaction equation

HRID 2190319 reaction equation
[S:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]=[C:2]1[NH:10]C(=O)C.O.[OH-].[Li+]>CO>[S:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]=[C:2]1[NH2:10]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrate2×HCID 15593545N-(thiazolo[4,5-c]pyridin-2-yl)acetamide

Product 1

HCID 14252938(1,3)Thiazolo(4,5-c)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of N-(thiazolo[4,5-c]pyridin-2-yl)acetamide, prepared in the previous step, in MeOH (200 mL) at room temperature was added lithium hydroxide hydrate (7.08 g, 169 mmol). The reaction mixture was stirred at room temperature for 30 min and then warmed to 40° C. After 3 h, additional lithium hydroxide hydrate (7.48 g) was added. The reaction mixture was heated to 50° C. for 20 h and concentrated. The reaction mixture was diluted with DCM/MeOH (˜10:1, 500 mL). The undissolved material was removed by filtration and the filtrate was concentrated. Purification by flash column chromatography on silica gel (eluted with 2% to 10% MeOH in DCM) gave thiazolo[4,5-c]pyridin-2-amine.

Workup

  1. temperaturewarmed to 40° C
  2. waitAfter 3 h
  3. temperatureThe reaction mixture was heated to 50° C. for 20 h
  4. concentrationconcentrated
  5. additionThe reaction mixture was diluted with DCM/MeOH (˜10:1, 500 mL)
  6. customThe undissolved material was removed by filtration
  7. concentrationthe filtrate was concentrated
  8. customPurification by flash column chromatography on silica gel (eluted with 2% to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-85f87b6daa354f8dbe35c680bc789d31
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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