Water → HCID 42645967, compound

HRID 38234Notes

Reaction equation

HRID 38234 reaction equation
COC1C=CC(C[N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[S:16][C:17]=3[C:18]#[N:19])[CH:10]=[N:9]2)=CC=1.C([O-])([O-])=O.[Na+].[Na+].O>C(O)(C(F)(F)F)=O>[NH:8]1[CH:12]=[C:11]([C:13]2[N:14]=[C:15]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[S:16][C:17]=2[C:18]#[N:19])[CH:10]=[N:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 86642332HCID 86642332, compound

Product 1

HCID 42645967HCID 42645967, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

According to Scheme 5 Step 3: A solution of 4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-(pyridin-2-ylamino)thiazol-5-carbonitrile (0.93 mmol, 360 mg) in TFA (3 mL) was microwaved for 5 min at 140° C. The reaction mixture was neutralized with a saturated solution of Na2CO3 (40 mL) and water (50 mL). The aqueous phase was filtered to afford a brown solid which was recrystallized thrice with DMF/water to yield 4-(1H-pyrazol-4-yl)-2-(pyridin-2-ylamino)thiazol-5-carbonitrile (0.24 mmol, 65 mg, 26%) as an off-white solid.

Workup

  1. filtrationThe aqueous phase was filtered
  2. customto afford a brown solid which
  3. customwas recrystallized thrice with DMF/water

Sources & evidence

ORD record
ord-33c151020d4c47249cbe42f2e9834dab
Source dataset
uspto-grants-2013_09
Patent number
US08524718B2

Reaction notes

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