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Pyridine → N-{6-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-yl}-2-(chloromethyl)-1,3-thiazole-4-carboxamide

HRID 1695737
Notes
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Reaction equation

HRID 1695737 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:21])[C:5]2[CH:6]=[N:7][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:9]=2[CH:10]=1.N1C=CC=CC=1.[Cl:28][CH2:29][C:30]1[S:31][CH:32]=[C:33]([C:35](Cl)=[O:36])[N:34]=1>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[S:11]([C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)(=[O:13])=[O:12])=[C:4]([NH:21][C:35]([C:33]2[N:34]=[C:30]([CH2:29][Cl:28])[S:31][CH:32]=2)=[O:36])[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 582557476-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-amineHCID 597024562-(Chloromethyl)-1,3-thiazole-4-carbonyl chloride2×

Product 1

HCID 58255773N-{6-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-yl}-2-(chloromethyl)-1,3-thiazole-4-carboxamideYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
3×

Conditions

Temperature
-10 °C

Procedure

A three necked rounded bottomed flask was charged with 6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-amine (12.7 g), anhydrous DCM (100 ml) and pyridine (7.5 ml) then placed under a nitrogen atmosphere and cooled to −10° C. A suspension of 2-(chloromethyl)-1,3-thiazole-4-carbonyl chloride (9.39 g) in anhydrous DCM (75 ml) was added in one portion. The reaction mixture was stirred at room temperature for ˜4 hrs. Additional 2-(chloromethyl)-1,3-thiazole-4-carbonyl chloride (1.36 g) in anhydrous DCM was added in one portion and the reaction was stirred overnight. The suspension was filtered, washing sparingly with DCM, then dried on the vacuum pump to give title compound (15.8 g).

Workup

  1. additionwas added in one portion
  2. stirringthe reaction was stirred overnight
  3. filtrationThe suspension was filtered
  4. washwashing sparingly with DCM
  5. customdried on the vacuum pump

Sources & evidence

ORD record
ord-22e62a23db4f441ca3b174e34677ea68
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08163743B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes