Potassium bis(trimethylsilyl)amide → HCID 178518575, compound

HRID 1250174Notes

Reaction equation

HRID 1250174 reaction equation
C1(S([CH2:9][N:10]2[C:14]([NH:15][C:16](=[O:25])[CH:17](Cl)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[N:12]=[N:11]2)=O)C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>O1CCCC1>[F:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[C:13]1[N:12]=[N:11][N:10]2[CH:9]=[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:16](=[O:25])[NH:15][C:14]=12

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 11408766n-[3-Benzenesulfinylmethyl-5-(2-fluorophenyl)-3h-1,2,3-triazol-4-yl]-2-chloro-2-phenylacetamide

Product 1

HCID 178518575HCID 178518575, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (−78° C.), stirred solution of N-[3-benzenesulfinylmethyl-5-(2-fluorophenyl)-3H-1,2,3-triazol-4-yl]-2-chloro-2-phenylacetamide (850 mg, 1.81 mmol) in dry tetrahydrofuran (50 ml) was added a solution of potassium bis(trimethylsilyl)amide (8.44 ml, 0.752 M in toluene, 6.34 mmol) and the reaction stirred for 90 minutes. The reaction was then transferred to a −20° C. bath and stirred for 15 minutes. The reaction was quenched by pouring into water (200 ml) and stirring for 10 minutes. The aqueous mixture was acidified with citric acid (10% aqueous) and extracted with ethyl acetate (2×200 ml). The combined organic extracts were washed with water (100 ml), brine (100 ml), dried (Na2SO4) and concentrated iin vacuo to about 10 ml total volume. 3-(2-Fluorophenyl)-6-phenyl-4H-1,2,3-triazolo[1,5-α]pyrimidin-5-one (355 mg, 64%) thus obtained was collected by filtration and washed with diethyl ether. The title product was used in subsequent reactions without further purification. δH (400 MHz, DMSO) 7.32-7.39 (6H, m, ArH, 7.70-7.74 (3H, m, ArH), 9.17 (1H, s, PhC═CH), 12.70 (1H, br s, NH); m/z (ES+) 307 (M+H+).

Workup

  1. customwas then transferred to a −20° C.
  2. stirringstirred for 15 minutes
  3. customThe reaction was quenched
  4. additionby pouring into water (200 ml)
  5. stirringstirring for 10 minutes
  6. extractionextracted with ethyl acetate (2×200 ml)
  7. washThe combined organic extracts were washed with water (100 ml), brine (100 ml)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated iin vacuo to about 10 ml total volume

Sources & evidence

ORD record
ord-19467926a11c430e91196f3a802a3fa0
Source dataset
uspto-grants-2002_01
Patent number
US06337331B1

Reaction notes

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