Methyl iodide → HCID 66970088, compound

HRID 1360337Notes

Reaction equation

HRID 1360337 reaction equation
[CH3:1][N:2]([CH3:29])[C@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[C:13]([C:14]3[O:15][C:16](=[O:28])[C:17]4[C:23]([CH2:24][CH3:25])=[CH:22][C:21]([O:26][CH3:27])=[CH:20][C:18]=4[N:19]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:4]1.[CH3:30]I>ClCCl>[C:16]([O-:28])(=[O:15])[CH3:17].[CH2:24]([C:23]1[C:17]2[C:16](=[O:28])[O:15][C:14]([C:13]3[C:8]([N:5]4[CH2:6][CH2:7][CH:3]([N+:2]([CH3:30])([CH3:1])[CH3:29])[CH2:4]4)=[N:9][CH:10]=[CH:11][CH:12]=3)=[N:19][C:18]=2[CH:20]=[C:21]([O:26][CH3:27])[CH:22]=1)[CH3:25]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 25205741AX-9657

Product 1

HCID 66970088HCID 66970088, compoundYield 156.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 132 (30 mg, 0.076 mmol) in dichloromethane (380 μL) was added methyl iodide (14.2 μL, 0.228 mmol) and the resulting mixture was stirred at ambient temperature for 2 hours. The solution was concentrated, and the residue was purified using preparative HPLC. The fractions containing the desired compound were lyophilized to yield compound 232 (27.8 mg, 89%) as a yellow powder. 1H NMR (CDCl3, 400 MHz) δ: 8.30 (dd, 1H, J=4.5 Hz), 8.11 (dd, 1H, J=1.6 Hz), 6.95 (d, 1H, J=2.4 Hz), 6.89 (m, 2H), 4.74 (m, 1H), 4.13 (m, 1H), 3.94 (s, 3H), 3.91 (m, 1H), 3.52 (m, 2H), 3.43 (s, 9H), 3.19 (m, 2H), 2.52 (m, 1H), 2.33 (m, 1H), 1.92 (s, 3H), 1.29 (t, 3H, J=7.5 Hz). ESMS m/z: 409.1 [M+]

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was purified
  3. additionThe fractions containing the desired compound

Sources & evidence

ORD record
ord-8676345a3eda4499827f87109f5e64aa
Source dataset
uspto-grants-2011_02
Patent number
US07879846B2

Reaction notes

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