Benzylamine → HCID 59408769, compound

HRID 1188109Notes

Reaction equation

HRID 1188109 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:10]1[S:11][C:12]([C:15]([NH:17][C:18]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[N:20](C(OC(C)(C)C)=O)[N:19]=2)=[O:16])=[CH:13][N:14]=1>O1CCOCC1>[CH2:1]([NH:8][C:10]1[S:11][C:12]([C:15]([NH:17][C:18]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[NH:20][N:19]=2)=[O:16])=[CH:13][N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 59408750HCID 59408750, compound

Product 1

HCID 59408769HCID 59408769, compoundYield 106.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

Benzylamine (0.1 mL, 0.87 mmol) was added to a solution of tert-butyl 3-(2-bromothiazole-5-carboxamido)-5-(4-fluorophenyl)-1H-pyrazole-1-carboxylate (160 mg, 0.43 mmol) in dioxane (3 mL). The resulting solution was stirred at 85° C. for 24 hrs. The solvent was evaporated and the crude product was purified by column (0-10% MeOH/AcOEt gradient), yielding 2-(benzylamino)-N-(5-(4-fluorophenyl)-1H-pyrazol-3-yl)thiazole-5-carboxamide (180 mg, 90%) as a solid.

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified by column (0-10% MeOH/AcOEt gradient)

Sources & evidence

ORD record
ord-b3db5c9f39374b52af28cbbed615f391
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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