Sodium Carbonate → HCID 46836808, compound

HRID 1520208Notes

Reaction equation

HRID 1520208 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][C:23]([F:26])=[CH:22][N:21]=4)[S:16][C:17]=3[F:18])[CH:10]=[N:9]2)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)(C(F)(F)F)=O>[F:18][C:17]1[S:16][C:15]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=2)=[N:14][C:13]=1[C:11]1[CH:12]=[N:8][NH:9][CH:10]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 86658561HCID 86658561, compound

Product 1

HCID 46836808HCID 46836808, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

According to Scheme 7 Step 2: A solution of N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-fluorothiazol-2-yl)-5-fluoropyridin-2-amine (1.85 mmol, 739 mg) in TFA (2 mL) was microwaved for 8 minutes at 120° C. The reaction mixture was neutralized with a saturated solution of Na2CO3 (100 mL). The aqueous phase was filtered to afford a brown solid. The resulting crude product was purified by flash chromatography over silica gel using DCM as eluent to yield 5-fluoro-N-(5-fluoropyridin-2-yl)-4-(1H-pyrazol-4-yl)thiazol-2-amine (0.21 mmol, 60 mg, 95%) as a yellow solid.

Workup

  1. filtrationThe aqueous phase was filtered
  2. customto afford a brown solid
  3. customThe resulting crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-f0623e8161f6482fa88112272968b7ea
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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