Trifluoroacetic acid → N-(6-amino-4-methylpyridin-2-yl)-2-(4-cyanophenyl)-4-methyl-1,3-thiazole-5-sulfonamide

HRID 2374456Notes

Reaction equation

HRID 2374456 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]([S:15]([NH:18][C:19]3[N:24]=[C:23]([NH:25]C(=O)OC(C)(C)C)[CH:22]=[C:21]([CH3:33])[CH:20]=3)(=[O:17])=[O:16])=[C:12]([CH3:14])[N:13]=2)=[CH:5][CH:4]=1)#[N:2].FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[NH2:25][C:23]1[N:24]=[C:19]([NH:18][S:15]([C:11]2[S:10][C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)=[N:13][C:12]=2[CH3:14])(=[O:17])=[O:16])[CH:20]=[C:21]([CH3:33])[CH:22]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 71045661HCID 71045661, compound

Product 1

HCID 12002964N-(6-amino-4-methylpyridin-2-yl)-2-(4-cyanophenyl)-4-methyl-1,3-thiazole-5-sulfonamideYield 83.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
24 °C

Procedure

To a solution of tert-butyl [6-({[2-(4-cyanophenyl)4-methyl-1,3-thiazol-5-yl]sulfonyl}amino)-4-methylpyridin-2-yl]carbamate (0.334 g, 0.68 mmol, 1 equiv) in dichloromethane (3 mL) was added trifluoroacetic acid (0.21 mL, 4 equiv). The reaction mixture was stirred at 24° C. for 48 h. The solution was neutralized with saturated aqueous sodium bicarbonate, and the resulting solution was extracted with dichloromethane (3×20 mL). The collected organic was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by high performance flash chromatography (0→1% methanol in dichloromethane) provided the titled product N-(6-Amino-4-methylpyridin-2-yl)-2-(4-cyanophenyl)-4-methyl-1,3-thiazole-5-sulfonamide (0.22 g, 81%). 1H NMR (400 MHz, DMSO-d6), δ: 12.08 (br s, 1H), 8.09 (d, J=8.3 Hz, 2H), 7.95 (d, J=8.3 Hz, 2H), 6.62 (br s, 2H), 6.12 (s, 1H), 5.79 (s, 1H), 2.59 (s, 3H), 2.08 (s, 3H); HRMS (ESI): Calculated for C17H16N5O2S2 m/z 386.0740. Found: 386.0745;. Anal. Calcd for C17H15N5O2S2: C, 52.97; H, 3.92; N, 18.17; Found: C, 52.75; H, 3.76; N, 18.03.

Workup

  1. extractionthe resulting solution was extracted with dichloromethane (3×20 mL)
  2. dry with materialThe collected organic was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by high performance flash chromatography (0→1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-16e93cf067224da49936908479be58d2
Source dataset
uspto-grants-2008_12
Patent number
US07462634B2

Reaction notes

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