[1,3]Thiazolo[5,4-b]pyridin-6-amine → HCID 44181665, compound

HRID 1911233Notes

Reaction equation

HRID 1911233 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[C:6]([C:19]([OH:21])=O)=[CH:5]2.[NH2:22][C:23]1[CH:24]=[C:25]2[N:31]=[CH:30][S:29][C:26]2=[N:27][CH:28]=1>>[N:31]1[C:25]2[C:26](=[N:27][CH:28]=[C:23]([NH:22][C:19]([C:6]3[N:7]([CH2:11][C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=4)[C:8]4[C:4]([CH:5]=3)=[CH:3][C:2]([F:1])=[CH:10][CH:9]=4)=[O:21])[CH:24]=2)[S:29][CH:30]=1

Participants

3

Reactant 2

HCID 53439226[1,3]Thiazolo[5,4-b]pyridin-6-amineHCID 574315135-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid

Product 1

HCID 44181665HCID 44181665, compoundYield 72.9%

Procedure

The process is performed according to a method similar to that of Example 1.2, starting with 0.32 g (1.11 mmol) of 5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid prepared in step 1.1 and 0.2021 g (1.34 mmol) of 6-amino-thiazolo[5,4-b]pyridine (WO2007/100758). At the end of the reaction, the product is concentrated under reduced pressure and then taken up in 100 mL of water. A precipitate is collected by filtration, and is purified by chromatography on a column of alumina, eluting with a mixture of dichloromethane and methanol. The resulting product is recrystallized from methanol, and a solid is collected by filtration and dried under reduced pressure. 340 mg of the expected product are thus isolated.

Workup

  1. customAt the end of the reaction
  2. concentrationthe product is concentrated under reduced pressure
  3. filtrationA precipitate is collected by filtration
  4. customis purified by chromatography on a column of alumina
  5. washeluting with a mixture of dichloromethane and methanol
  6. customThe resulting product is recrystallized from methanol
  7. filtrationa solid is collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-c6462eb9d1ff47fe93b4e5038c6515b2
Source dataset
uspto-grants-2013_12
Patent number
US08604050B2

Reaction notes

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