Sodium Bicarbonate → HCID 58456164, compound

HRID 410676Notes

Reaction equation

HRID 410676 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[S:23][C:22]([C:24]3(O)[CH2:29][CH2:28][S:27](=[O:31])(=[O:30])[CH2:26][CH2:25]3)=[N:21][CH:20]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1.CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C([O-])(O)=O.[Na+]>O>[O:31]=[S:27]1(=[O:30])[CH2:26][CH:25]=[C:24]([C:22]2[S:23][C:19]([C:4]3[CH:5]=[C:6]([NH:8][C:9]4[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=4)[CH:7]=[C:2]([CH3:1])[CH:3]=3)=[CH:20][N:21]=2)[CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 672587064-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]tetrahydro-2H-thiopyran-4-ol 1,1-dioxideHCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Product 1

HCID 58456164HCID 58456164, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

The product from Step 1 (210 mg, 0.433 mmol) was combined with Eaton's reagent (1.00 ml, 6.30 mmol) and stirred at 100° C. for 16 hrs. The reaction was cooled to room temperature and slowly neutralized with aqueous saturated NaHCO3 (4 mL). It was then diluted with water (4 mL) and extracted with EtOAc (2×15 mL). The combined organic layers were washed with brine, dried (MgSO4), and evaporated. Upon addition of CH2Cl2, the title compound precipitated and was isolated by filtration (0.185 g, 0.397 mmol, 91% yield). MS ESI: [M+H]+ m/z 467.0. 1H NMR (500 MHz, DMSO-d6) δ 10.29 (s, 1H), 8.83 (d, J=4.9, 1H), 8.12 (d, J=2.7, 1H), 8.03 (bs, 1H), 7.47 (bs, 1H), 7.29 (d, J=4.9, 1H), 7.21 (bs, 1H), 6.53 (m, 1H), 4.00 (m, 2H), 3.39 (m, 2H), 3.14 (m, 2H), 2.32 (s, 3H). rhSYK activity=+++.

Workup

  1. extractionextracted with EtOAc (2×15 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. additionUpon addition of CH2Cl2
  6. customthe title compound precipitated
  7. customwas isolated by filtration (0.185 g, 0.397 mmol, 91% yield)

Sources & evidence

ORD record
ord-669cf365fb704009a074f8d69decb73a
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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