Methyl iodide → HCID 71679218, compound

HRID 69528Notes

Reaction equation

HRID 69528 reaction equation
[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=3[Cl:25])(=[O:16])=[O:15])[CH2:11][N:10]2[C:26]([C:28]2([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][N:33]=3)[CH2:31][NH:30][CH2:29]2)=[O:27])=[O:8])[CH2:5][CH2:4]1)#[N:2].[CH3:39]I>CO>[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=3[Cl:25])(=[O:15])=[O:16])[CH2:11][N:10]2[C:26]([C:28]2([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][N:33]=3)[CH2:31][N:30]([CH3:39])[CH2:29]2)=[O:27])=[O:8])[CH2:4][CH2:5]1)#[N:2]

Participants

4

Reactant 2

HCID 6328Methyl iodide2×HCID 71679217HCID 71679217, compound

Product 1

HCID 71679218HCID 71679218, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of example 2 (0.05 g, 86.4 μmol, Eq: 1.00) in refluxing methanol (1 ml) was added methyl iodide (9.2 mg, 4.05 μl, 64.8 μmol, Eq: 0.75). After complete addition the mixture was stirred at 80° C. for 2 h. Additional methyl iodide (9.2 mg, 4.05 μl, 64.8 μmol, Eq: 0.75) was added and the mixture was stirred at 80° C. for 2 h, then at 20° C. over night. The mixture was purified by preparative HPLC to yield a colorless solid (3 mg; 6%). m/z=592.2 [M+H]+.

Workup

  1. additionAfter complete addition the mixture
  2. stirringthe mixture was stirred at 80° C. for 2 h
  3. waitat 20° C. over night
  4. customThe mixture was purified by preparative HPLC
  5. customto yield a colorless solid (3 mg; 6%)

Sources & evidence

ORD record
ord-26da4f3f901c4c03ab4767f9aaffb2c7
Source dataset
uspto-grants-2014_09
Patent number
US08822505B2

Reaction notes

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