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

HRID 579788

Reaction equation

HRID 579788 reaction equation
N(C1C=CC2OCCOC=2C=1)=C=S.[C:14]([N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][NH2:24])[CH2:19][CH2:18]1)(=[O:16])[CH3:15].CS[C:27]1[S:28][C:29]2[C:34]([N:35]=1)=[CH:33][CH:32]=[CH:31][N:30]=2>>[C:14]([N:17]1[CH2:18][CH2:19][CH:20]([CH2:23][NH:24][C:27]2[S:28][C:29]3[C:34]([N:35]=2)=[CH:33][CH:32]=[CH:31][N:30]=3)[CH2:21][CH2:22]1)(=[O:16])[CH3:15]

Participants

4

Reactant 3

HCID 6998402-(Methylthio)thiazolo[5,4-b]pyridineHCID 27761732,3-Dihydro-1,4-benzodioxin-6-yl isothiocyanateHCID 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 fractions 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 fractions were collected
  4. customthe eluent was evaporated

Sources & evidence

ORD record
ord-18f857e80ac7404e92acdc90022a1021
Source dataset
uspto-grants-1988_06
Patent number
US04749702

Linked notes

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