Pyridine → HCID 44539936, compound

HRID 1695798Notes

Reaction equation

HRID 1695798 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:12]=[C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[N:15][CH:16]=2)[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2S(C1C=CC=CC=1)(=O)=O.N1C=CC=CC=1.[CH3:37][C:38]1[S:39][CH:40]=[C:41]([C:43](Cl)=[O:44])[N:42]=1>C(Cl)Cl>[CH3:37][C:38]1[S:39][CH:40]=[C:41]([C:43]([NH:1][C:2]2[CH:10]=[C:9]([C:11]3[CH:16]=[N:15][CH:14]=[C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:12]=3)[CH:8]=[C:7]3[C:3]=2[CH:4]=[N:5][NH:6]3)=[O:44])[N:42]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 211839592-Methyl-1,3-thiazole-4-carbonyl chloride3×HCID 58255824HCID 58255824, compound

Product 1

HCID 44539936HCID 44539936, compoundYield 18.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-{5-[4-Amino-1-(phenylsulfonyl)-1H-indazol-6-yl]-3-pyridinyl}methanesulfonamide (50 mg) was dissolved in DCM (1 ml) and pyridine (0.014 ml) was added. A solution of 2-methyl-1,3-thiazole-4-carbonyl chloride (22 mg) in DCM (1 ml) was added to the reaction and the mixture was stirred at RT for 30 min. Further 2-methyl-1,3-thiazole-4-carbonyl chloride (10 mg) was added to the reaction and stirring continued for 30 min. Further 2-methyl-1,3-thiazole-4-carbonyl chloride (40 mg) was added then the reaction was quenched with water and passed through a hydrophobic frit. The organic layer was evaporated to dryness and the residue was dissolved in DMSO:MeOH (1 ml, 1:1, v/v) and purified by MDAP (method E). The compound was dissolved in MeOH containing a few drops of 2M NaOH and stirred for 5 mins at RT. The residue was dissolved in MeOH and loaded onto an SAX SPE cartridge pre-conditioned with MeOH. After eluting with MeOH and evaporating to dryness, the residue was dissolved in DMSO and purified by MDAP (method E) to give the title compound (9 mg).

Workup

  1. stirringstirring
  2. waitcontinued for 30 min
  3. customthe reaction was quenched with water
  4. customThe organic layer was evaporated to dryness
  5. dissolutionthe residue was dissolved in DMSO
  6. customMeOH (1 ml, 1:1, v/v) and purified by MDAP (method E)
  7. dissolutionThe compound was dissolved in MeOH containing a few drops of 2M NaOH
  8. stirringstirred for 5 mins at RT
  9. dissolutionThe residue was dissolved in MeOH
  10. washAfter eluting with MeOH
  11. customevaporating to dryness
  12. dissolutionthe residue was dissolved in DMSO
  13. custompurified by MDAP (method E)

Sources & evidence

ORD record
ord-c7cb0f6b7c474da2a7c1ab2f6f2a141d
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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