Methyl iodide → HCID 59174878, compound

HRID 1177632Notes

Reaction equation

HRID 1177632 reaction equation
FC(F)(F)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]3[C:19]([N:20]=2)=[CH:18][CH:17]=[C:16]([C:21]2([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:23][CH2:22]2)[N:15]=3)=[C:8]([F:30])[CH:7]=1)=O.CI.[CH:35]([N-]C(C)C)(C)C.[Li+]>C1COCC1.C(Cl)Cl>[F:30][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=1[C:12]1[S:13][C:14]2[C:19]([N:20]=1)=[CH:18][CH:17]=[C:16]([C:21]1([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:23][CH2:22]1)[N:15]=2)[N:5]([CH3:3])[CH3:35]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 59174914HCID 59174914, compound

Product 1

HCID 59174878HCID 59174878, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2,2,2-Trifluoro-N-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)acetamide (80 mg, 0.175 mmol) was dissolved in THF (1.7 mL) before methyl iodide (13 μl, 0.210 mmol) and lithium diisopropylamide (175 μl, 0.350 mmol) were added and stirred at 0° C. for 30 min. The reaction mixture was diluted with 75 mL of DCM, added to a separatory funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed 2 times with 50 mL of water, separated, dried over sodium sulfate, and concentrated via rotovap to give the title compound after flash chromatography. MS (ESI) m/z: Calculated: 389.1; Observed: 390.1 (M++1).

Workup

  1. additionwere added
  2. additionadded to a separatory funnel
  3. custompartitioned with sodium bicarbonate (saturated, aqueous)
  4. washwashed 2 times with 50 mL of water
  5. customseparated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated via rotovap

Sources & evidence

ORD record
ord-7067d92ab9be45dab62316eed273f72f
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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