Pyridine → N-(6-{6-Chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide

HRID 1695802Notes

Reaction equation

HRID 1695802 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]2S(C1C=CC=CC=1)(=O)=O.N1C=CC=CC=1.[CH3:38][C:39]1[S:40][CH:41]=[C:42]([C:44](Cl)=[O:45])[N:43]=1>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][NH:6]3)=[C:2]([NH:1][C:44]([C:42]3[N:43]=[C:39]([CH3:38])[S:40][CH:41]=3)=[O:45])[CH:10]=2)=[CH:12][C:13]=1[NH:18][S:19]([CH3:22])(=[O:20])=[O:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 211839592-Methyl-1,3-thiazole-4-carbonyl chlorideHCID 58255829N-{5-[4-Amino-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-chloro-3-pyridinyl}methanesulfonamide

Product 1

HCID 44539723N-(6-{6-Chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamideYield 34.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-{5-[4-Amino-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-chloro-3-pyridinyl}methane sulfonamide (100 mg) was dissolved in DCM (5 ml) and pyridine (0.02 ml) was added. 2-Methyl-1,3-thiazole-4-carbonyl chloride (41 mg) was added and the reaction stirred at RT for 1 h. The reaction was evaporated to dryness and the residue was stirred in MeOH:2M NaOH (aq) (5 ml, 1:1, v/v) for 15 min. The reaction was neutralised with 2M HCl and evaporated to dryness. The residue was dissolved in DMSO (1 ml), filtered and purified by MDAP (method E). The pure fraction was evaporated to dryness to give title compound (33 mg).

Workup

  1. customThe reaction was evaporated to dryness
  2. stirringthe residue was stirred in MeOH
  3. wait2M NaOH (aq) (5 ml, 1:1, v/v) for 15 min
  4. customevaporated to dryness
  5. dissolutionThe residue was dissolved in DMSO (1 ml)
  6. filtrationfiltered
  7. custompurified by MDAP (method E)
  8. customThe pure fraction was evaporated to dryness

Sources & evidence

ORD record
ord-8927739e4abb464e83142c1702d7d047
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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