HCID 59408769, compound → HCID 25001105, compound

HRID 1188110Notes

Reaction equation

HRID 1188110 reaction equation
[CH2:1]([NH:8][C:9]1[S:10][C:11]([C:14]([NH:16][C:17]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[NH:19][N:18]=2)=O)=[CH:12][N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1>[CH2:1]([NH:8][C:9]1[S:10][C:11]([CH2:14][NH:16][C:17]2[CH:21]=[C:20]([C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[NH:19][N:18]=2)=[CH:12][N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 59408769HCID 59408769, compound

Product 1

HCID 25001105HCID 25001105, compoundYield 119.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

BMS was added to a solution of 2-(benzylamino)-N-(5-(4-fluorophenyl)-1H-pyrazol-3-yl)thiazole-5-carboxamide (50 mg, 0.13 mmol) in THF (1 mL). The resulting solution was stirred at RT overnight. The reaction was then quenched with MeOH (0.5 mL) and 1N HCl was added until pH=2. After stirring the reaction mixture at RT for 3 hrs, the organic solvents were evaporated and the aqueous solution was neutralized with a NaHCO3 saturated aqueous solution, extracted with AcOEt, dried with Na2SO4 and concentrated. The crude product was purified by column (0-2% MeOH/AcOEt gradient), yielding N-benzyl-5-((5-(4-fluorophenyl)-1H-pyrazol-3-ylamino)methyl)thiazol-2-amine (59 mg, 98%).

Workup

  1. customThe reaction was then quenched with MeOH (0.5 mL) and 1N HCl
  2. additionwas added until pH=2
  3. stirringAfter stirring the reaction mixture at RT for 3 hrs
  4. customthe organic solvents were evaporated
  5. extractionextracted with AcOEt
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated
  8. customThe crude product was purified by column (0-2% MeOH/AcOEt gradient)

Sources & evidence

ORD record
ord-e556e6de88864f49a69f16d4f44439c9
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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