Sodium Carbonate → HCID 46836729, compound

HRID 1520196Notes

Reaction equation

HRID 1520196 reaction equation
COC1C=CC(C[N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([I:26])[N:21]=4)[S:16][C:17]=3[CH3:18])[CH:10]=[N:9]2)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)(C(F)(F)F)=O>[I:26][C:22]1[N:21]=[C:20]([NH:19][C:15]2[S:16][C:17]([CH3:18])=[C:13]([C:11]3[CH:12]=[N:8][NH:9][CH:10]=3)[N:14]=2)[CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 86658549HCID 86658549, compound

Product 1

HCID 46836729HCID 46836729, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

According to Scheme 2 Step 5: A solution of N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-methylthiazol-2-yl)-6-iodopyridin-2-amine (0.27 mmol, 136 mg) in TFA (1.4 mL) was microwaved for 5 minutes at 140° C. The reaction mixture was neutralized with a saturated solution of Na2CO3 and the aqueous phase was extracted with DCM. The organic phase was dried over MgSO4, was filtered and was concentrated. The resulting crude product was purified by flash chromatography over silica gel using DCM/MeOH (100:0 to 90:10) as eluent to yield N-(6-iodopyridin-2-yl)-5-methyl-4-(1H-pyrazol-4-yl)thiazol-2-amine (91 μmol, 34 mg, 34%) as a white solid.

Workup

  1. extractionthe aqueous phase was extracted with DCM
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationwas filtered
  4. concentrationwas concentrated
  5. customThe resulting crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-4a5ddc26561841e296be9813a51a63eb
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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