Methyl iodide → HCID 11531637, compound

HRID 732150Notes

Reaction equation

HRID 732150 reaction equation
[Li][CH2:2]CCC.C(NC(C)C)(C)C.[Cl:13][C:14]1[CH:15]=[C:16]([C:20]2[O:24][N:23]=[C:22]([CH:25]([N:27]([CH3:40])[C:28]3[N:32]([CH3:33])[C:31]([C:34]4[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=4)=[N:30][N:29]=3)[CH3:26])[N:21]=2)[CH:17]=[CH:18][CH:19]=1.CI>O>[Cl:13][C:14]1[CH:15]=[C:16]([C:20]2[O:24][N:23]=[C:22]([C:25]([N:27]([CH3:40])[C:28]3[N:32]([CH3:33])[C:31]([C:34]4[CH:35]=[CH:36][N:37]=[CH:38][CH:39]=4)=[N:30][N:29]=3)([CH3:2])[CH3:26])[N:21]=2)[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 11718181HCID 11718181, compoundHCID 178418339Butyllithium

Product 1

HCID 11531637HCID 11531637, compound

Reagents, catalysts & solvents 1

HCID 962WaterCatalyst

Conditions

Temperature
0 °C

Procedure

n-BuLi (132 ml 2.5 M in hex., 0.33 mmol) was added to diisopropyl amine (55 ml, 0.39 mmol). After stirring for 20 minutes at 0° C. the mixture was cooled to −78° C. and N-{1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethyl}-N,4-dimethyl-5-pyridin-4-yl-4H-1,2,4-triazol-3-amine (110 mg, 0.28 mmol) was added. After 15 min. methyl iodide (20 μl, 0.33 mmol) was added and the temperature was raised to r.t. After stirring for 2 h five drops of water were added. After solvent removal in vacuo, the crude was taken up in DCM, washed with water and brine, dried and concentrated. The desired product was obtained by prep. HPLC in 20 mg yield. 1H NMR: 1.7 (s, 6 H) 2.8 (s, 3 H) 3.8 (s, 3 H) 7.5 (t, 1 H) 7.6 (d, 1 H) 7.7 (s, 2 H) 8.0 (d, 1 H) 8.1 (s, 1 H) 8.8 (s, 2 H)

Workup

  1. temperaturewas cooled to −78° C.
  2. temperaturethe temperature was raised to r.t
  3. additionwere added
  4. customAfter solvent removal in vacuo
  5. washwashed with water and brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-63a4507d768e47f18622c2b328c8656b
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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