Pyridine → N-[6-bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide

HRID 520576Notes

Reaction equation

HRID 520576 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:17])[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH:6]=2.N1C=CC=CC=1.[CH3:24][C:25]1[S:26][CH:27]=[C:28]([C:30](Cl)=[O:31])[N:29]=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:17][C:30]([C:28]2[N:29]=[C:25]([CH3:24])[S:26][CH:27]=2)=[O:31])[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH:6]=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 211839592-Methyl-1,3-thiazole-4-carbonyl chlorideHCID 582557836-Bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine

Product 1

HCID 58255778N-[6-bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round bottom flask was introduced 6-bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (2.77 g) dissolved in DCM (120 ml) followed by the addition of pyridine (1.135 ml). The reaction mixture was left to stir for a few minutes before the addition of 2-methyl-1,3-thiazole-4-carbonyl chloride (2.267 g). The reaction mixture was left to stir at RT for 1 h. After this time the reaction mixture was extracted between DCM and saturated sodium bicarbonate aq. The extracted organic layer was dried down. The crude was dissolved in DCM and adsorbed onto fluorisil before purification by solid loading on companion using Si Column (40 g) eluting with 40-100% ethyl acetate in cyclohexane. The appropriate fractions were combined and evaporated to dryness to yield the title compound, 2.6 g.

Workup

  1. waitThe reaction mixture was left
  2. waitThe reaction mixture was left
  3. extractionAfter this time the reaction mixture was extracted between DCM and saturated sodium bicarbonate aq. The extracted organic layer
  4. customwas dried down
  5. dissolutionThe crude was dissolved in DCM
  6. customadsorbed onto fluorisil before purification by solid loading on companion
  7. washeluting with 40-100% ethyl acetate in cyclohexane
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-9eec165030c54e4aa8f4f4141b9fa513
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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