2-(Methylthio)thiazolo[5,4-b]pyridine → 1-acetyl-N-(thiazolo[5,4-b]pyridin-2-yl)-4-piperidinemethanamine

HRID 1761484

Reaction equation

HRID 1761484 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][NH2:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].CS[C:14]1[S:15][C:16]2[C:21]([N:22]=1)=[CH:20][CH:19]=[CH:18][N:17]=2>>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([CH2:10][NH:11][C:14]2[S:15][C:16]3[C:21]([N:22]=2)=[CH:20][CH:19]=[CH:18][N:17]=3)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 6998402-(Methylthio)thiazolo[5,4-b]pyridineHCID 126870221-(4-(Aminomethyl)piperidin-1-yl)ethan-1-one

Product 1

HCID 212415751-acetyl-N-(thiazolo[5,4-b]pyridin-2-yl)-4-piperidinemethanamineYield 93%

Conditions

Temperature
140 °C

Procedure

A mixture of 11 parts of 1-acetyl-4-piperidinemethanamine and 9 parts of 2-(methylthio)thiazolo[5,4-b]pyridine was stirred and heated for 20 hours at 140° C. The whole was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fraction were collected and the eluent was evaporated, yielding 13.5 parts (93%) of 1-acetyl-N-(thiazolo[5,4-b]pyridin-2-yl)-4-piperidinemethanamine as a residue (intermediate 51).

Workup

  1. customThe whole was purified by column chromatography over silica gel using
  2. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  3. customThe pure fraction were collected
  4. customthe eluent was evaporated

Sources & evidence

ORD record
ord-0511f177e2ef482184d5dc07c422513e
Source dataset
uspto-grants-1989_05
Patent number
US04826848

Linked notes

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