Sodium methanethiolate → HCID 11739862, compound

HRID 1160106Notes

Reaction equation

HRID 1160106 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([O:9][CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[O:12])[N:3]=1.[CH3:24][S-:25].[Na+]>C(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([S:25][CH3:24])[N:5]=[C:4]([O:9][CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[O:12])[N:3]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 58964644HCID 58964644, compound

Product 1

HCID 11739862HCID 11739862, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 25 mL recovery flask was added 2-(4-Amino-6-chloro-[1,3,5]triazin-2-yloxy)-N-(3-trifluoromethyl-phenyl)-acetamide (33 mg, 0.0950 mmol, 1.0 eq.) and CH2Cl2 (7 mL). Sodium thiomethoxide (20 mg, 0.285 mmol, 3.0 eq.) was added and the resulting solution was stirred at room temperature for 1 h. The reaction was diluted with CH2Cl2 (50 mL) and washed with H2O (1×50 mL) and brine (1×50 mL). The combined aqueous phases were extracted with CH2Cl2 (2×25 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated to give a brown solid. The crude material was purified via preparative HPLC to give 2-(4-Amino-6-methylsulfanyl-[1,3,5]triazin-2-yloxy)-N-(3-trifluoromethyl-phenyl)-acetamide as a white solid (6.2 mg, 24% yield). LC/MSD (HP Series 1100 MSD) Expected MW: 359.07, Observed M+H, 360.1, Retention time: 1.40. Analytical LC: 98%, Retention time: 4.87 (11 minute run). 1H-NMR, CH3OH-d4, Varian 400 MHz δ 8.01 (s, 1H), 7.81 (d, 1H), 7.51 (t, 1H), 7.40 (d, 1H), 4.94 (s, 2H), 2.46 (3H) ppm.

Workup

  1. washwashed with H2O (1×50 mL) and brine (1×50 mL)
  2. extractionThe combined aqueous phases were extracted with CH2Cl2 (2×25 mL)
  3. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a brown solid
  7. customThe crude material was purified via preparative HPLC

Sources & evidence

ORD record
ord-40949b6f1bfd42c2bf35a4e07b886fcf
Source dataset
uspto-grants-2010_10
Patent number
US07816353B2

Reaction notes

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