HCID 67433522, compound → HCID 46837064, compound

HRID 1520228Notes

Reaction equation

HRID 1520228 reaction equation
C(NC[N:6]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)[C:7]1[S:8][C:9]([CH3:22])=[C:10]([C:12]2[CH:13]=[N:14][N:15]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[CH:16]=2)[N:11]=1)(=O)C>Cl>[CH3:22][C:9]1[S:8][C:7]([NH:6][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[N:11][C:10]=1[C:12]1[CH:13]=[N:14][N:15]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[CH:16]=1

Participants

3

Reactant 1

HCID 67433522HCID 67433522, compound

Product 1

HCID 46837064HCID 46837064, compoundYield 73,333.297%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

According to Scheme 22, Step 2: A solution of N-((4-(2-((acetamidomethyl)(pyridin-2-yl)amino)-5-methylthiazol-4-yl)-1H-pyrazol-1-yl)methyl)acetamide (75 μmol, 30 mg) in 1 mL of HCl (1 N) was stirred at room temperature for 1 hour. The solution was then basified to pH 8 and the aqueous phase was extracted with AcOEt. The organic phases were dried over MgSO4, were filtered and were concentrated. The crude compound was purified by flash chromatography with silica gel using DCM/MeOH (100:0 to 95:5) and then by SCX-2 with a catch and release methodology to afford N-((4-(5-methyl-2-(pyridin-2-ylamino)thiazol-4-yl)-1H-pyrazol-1-yl)methyl)acetamide (55 mmol, 18 mg, 73%) as a beige solid.

Workup

  1. extractionthe aqueous phase was extracted with AcOEt
  2. dry with materialThe organic phases were dried over MgSO4
  3. filtrationwere filtered
  4. concentrationwere concentrated
  5. customThe crude compound was purified by flash chromatography with silica gel

Sources & evidence

ORD record
ord-b5de1b5acaa0458f83b1e173e2b65afd
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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