3-Chloro-6-fluorobenzo[b]thiophene-2-carbonyl chloride → 3-((4-(3-chloro-6-fluorobenzo[b]thiophene-2-carboxamido)phenyl)amino)-5-((4-hydroxybenzyl)amino)-1H-pyrazole-4-carboxamide

HRID 1405110Notes

Reaction equation

HRID 1405110 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:13]([C:14]([NH2:16])=[O:15])=[C:12]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[NH:11][N:10]=2)=[CH:4][CH:3]=1.[Cl:26][C:27]1[C:28]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:29]=2[S:30][C:31]=1[C:32](Cl)=[O:33]>CN(C=O)C>[Cl:26][C:27]1[C:28]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:29]=2[S:30][C:31]=1[C:32]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[C:13]([C:14]([NH2:16])=[O:15])=[C:12]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[NH:11][N:10]=2)=[CH:6][CH:7]=1)=[O:33]

Participants

4

Reactant 2

HCID 27831733-Chloro-6-fluorobenzo[b]thiophene-2-carbonyl chlorideHCID 178513736HCID 178513736, compound

Product 1

HCID 1785137373-((4-(3-chloro-6-fluorobenzo[b]thiophene-2-carboxamido)phenyl)amino)-5-((4-hydroxybenzyl)amino)-1H-pyrazole-4-carboxamideYield 6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-((4-aminophenyl)amino)-5-((4-hydroxybenzyl)amino)-1H-pyrazole-4-carboxamide (100 mg) was dissolved in 3.0 mL of DMF and TEA (125 μL, 3.0 eq.) was then added to the reaction vessel. Reaction was then stirred on an ice bath for 15 min and 3-Chloro-6-fluorobenzo[b]thiophene-2-carbonyl chloride (75 mg, 1.00 eq.) dissolved in DMF (2.0 mL) was slowly added into the reaction. The reaction continued stirring for 18 hrs and allowed to reach room temperature. The reaction was tracked via HPLC, once completed and no traces of starting material is present, the solvent was then removed via vacuo and column chromatography was used to purify the compound. A gradient of 0 to 20% MeOH in dichloromethane was used and the desired fractions were combined, evaporated and triturated with diisoproyl ether then filtered to yield product as an off white powder (0.008 g, 6.0% yield).

Workup

  1. customReaction
  2. additionwas slowly added into the reaction
  3. stirringThe reaction continued stirring for 18 hrs
  4. customto reach room temperature
  5. customthe solvent was then removed via vacuo and column chromatography
  6. customto purify the compound
  7. customevaporated
  8. customtriturated with diisoproyl ether
  9. filtrationthen filtered

Sources & evidence

ORD record
ord-f22fbf7666be47f89114523708e4ca55
Source dataset
uspto-grants-2014_12
Patent number
US08916555B2

Reaction notes

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