Sulfuric Acid → HCID 86723394, compound

HRID 508550Notes

Reaction equation

HRID 508550 reaction equation
C([O:3][CH:4](OCC)[C:5]1[N:10]=[C:9]([CH2:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)[C:8]([F:17])=[C:7]([NH:18]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=1)C.OS(O)(=O)=O.CC#N>O>[NH2:18][C:7]1[C:8]([F:17])=[C:9]([CH2:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)[N:10]=[C:5]([CH:4]=[O:3])[CH:6]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 86723395HCID 86723395, compound

Product 1

HCID 86723394HCID 86723394, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Following the procedure of Example 12, 6-(diethoxymethyl)-3-fluoro-2-(thiazol-2-ylmethyl)-N-tritylpyridin-4-amine (471 mg, 0.85 mmol), conc H2SO4 (0.5 mL), CH3CN (10 mL) and H2O (10 mL) gave the title compound (0.145 g, 71%) as an off-white solid: 1H NMR (400 MHz, CDCl3) δ 9.88 (s, 1H), 7.72 (d, J=3.3 Hz, 1H), 7.28 (d, J=6.7 Hz, 1H), 7.26 (d, J=3.4 Hz, 1H), 4.59 (d, J=2.8 Hz, 2H), 4.56 (br s, 2H); 19F NMR (376 MHz, DMSO-d6) δ −142.44; HRMS-ESI (m/z) [M+H]+ calcd for C10H8FN3OS, 237.0372. found, 237.0363.

Sources & evidence

ORD record
ord-e00a5bf1ba7e4970919b9ba51f3f70be
Source dataset
uspto-grants-2015_08
Patent number
US09096526B2

Reaction notes

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