Tetrahydrofuran → HCID 59333290, compound

HRID 1893459Notes

Reaction equation

HRID 1893459 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]1[C:13]([C:16]#[C:17]C(=O)C(C)(C)C)=[CH:14]N=[C:8]1[C:7]([NH:24][CH2:25][CH2:26][CH2:27][OH:28])=[N:6]2.[Si](C=[N+]=[N-])(C)(C)[CH3:32].[Cl-:38].[NH4+:39].[O:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1>>[Cl:38][C:17]#[C:16][C:13]1[N:9]2[C:10]3[C:5]([N:6]=[C:7]([NH:24][CH2:25][CH2:26][CH2:27][O:28][CH:44]4[CH2:43][CH2:42][CH2:41][CH2:32][O:40]4)[C:8]2=[N:39][CH:14]=1)=[CH:4][C:3]([C:2]([F:30])([F:1])[F:29])=[CH:12][CH:11]=3

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 167693TrimethylsilyldiazomethaneHCID 68665608HCID 68665608, compound

Product 1

HCID 59333290HCID 59333290, compoundYield 48%

Conditions

Temperature
60 °C

Procedure

To a solution of 1-{7-(trifluoromethyl)-4-[(3-hydroxypropyl)amino]imidazo[1,2-a]quinoxalin-1-yl}-4,4-dimethylpent-1-yn-3-one (23 mg, 0.05 mmol) in anhydrous tetrahydrofuran (1 mL) was added TMS-diazomethane (2M in THF, 91 μL, 0.183 mmol). The mixture was stirred at 60° C. under argon for 6 h and then at room temperature overnight. The reaction mixture was treated with a saturated aqueous solution of ammonium chloride and extracted twice with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and evaporated. The crude product was purified by preparative TLC (silica gel, dichloromethane/methanol 20/1) to afford the title compound (12 mg, 48%) as a yellow oil.

Workup

  1. customat room temperature
  2. customovernight
  3. extractionextracted twice with dichloromethane
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by preparative TLC (silica gel, dichloromethane/methanol 20/1)

Sources & evidence

ORD record
ord-49dd1c672c2f49a48e2dea8af17fc65c
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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