Pyridine → HCID 44539724, compound

HRID 1695800Notes

Reaction equation

HRID 1695800 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:12]=[C:13]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[C:14]([Cl:17])=[N:15][CH:16]=2)[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH3:23].N1C=CC=CC=1.[CH3:30][C:31]1[S:32][CH:33]=[C:34]([C:36](Cl)=[O:37])[N:35]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:17][C:14]1[N:15]=[CH:16][C:11]([C:9]2[CH:8]=[C:7]3[C:3]([CH:4]=[N:5][N:6]3[CH3:23])=[C:2]([NH:1][C:36]([C:34]3[N:35]=[C:31]([CH3:30])[S:32][CH:33]=3)=[O:37])[CH:10]=2)=[CH:12][C:13]=1[NH:18][S:19]([CH3:22])(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 211839592-Methyl-1,3-thiazole-4-carbonyl chlorideHCID 86653304HCID 86653304, compound

Product 1

HCID 44539724HCID 44539724, compoundYield 1.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

N-[5-(4-Amino-1-methyl-1H-indazol-6-yl)-2-chloro-3-pyridinyl]methanesulfonamide (75 mg) was dissolved in DCM (2 ml) and pyridine (0.052 ml) was added followed by 2-methyl-1,3-thiazole-4-carbonyl chloride (52 mg) in DCM (1 ml) as a suspension. The reaction was stirred at RT for 1 h. Saturated sodium bicarbonate solution was added followed by DCM (3 ml) and the reaction was stirred vigorously. The reaction was passed through a hydrophobic frit and evaporated to dryness. The residue was dissolved in DMSO:MeOH (1:1, v/v, 1 ml) and purified by MDAP (method E) to give the title compound (1.5 mg).

Workup

  1. stirringthe reaction was stirred vigorously
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in DMSO:MeOH (1:1, v/v, 1 ml)
  4. custompurified by MDAP (method E)

Sources & evidence

ORD record
ord-44ad09fa1b1142dbb9f3187d03e2f4b8
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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