Water → HCID 67313923, compound

HRID 2179720Notes

Reaction equation

HRID 2179720 reaction equation
[H-].[Na+].[ClH:3].[N:4]12[CH2:11][CH2:10][CH:7]([CH2:8][CH2:9]1)[C@@H:6]([NH:12][C:13]([C:15]1[O:16][C:17]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH3:31])=[CH:22][CH:21]=[CH:20][C:18]=3[CH:19]=1)=[O:14])[CH2:5]2.I[CH3:33].O>CN(C=O)C>[Cl-:3].[CH3:31][O:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:23]1[C:17]2[O:16][C:15]([C:13]([NH:12][C@@H:6]3[CH:7]4[CH2:8][CH2:9][N+:4]([CH3:33])([CH2:11][CH2:10]4)[CH2:5]3)=[O:14])=[CH:19][C:18]=2[CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67312922HCID 67312922, compound

Product 1

HCID 67313923HCID 67313923, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-20 °C

Procedure

60.5 mg (1.51 mmol) of sodium hydride (60% suspension in mineral oil) are added to a solution, cooled to −20° C., of 250 mg (0.61 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-(2-methoxyphenyl)-1-benzofuran-2-carboxamide hydrochloride (Example 102) in 2.5 ml of DMF. After 30 min at room temperature and renewed cooling to −20° C., 33.9 μl (0.54 mmol) of iodomethane are added. After 18 h at room temperature, the reaction is stopped by adding water. The reaction mixture is purified by preparative HPLC. The product fractions are concentrated, codistilled with 1N hydrochloric acid, again concentrated and dried under high vacuum. 206 mg (79.7% of theory) of the title compound are obtained.

Workup

  1. waitAfter 18 h at room temperature
  2. customThe reaction mixture is purified by preparative HPLC
  3. concentrationThe product fractions are concentrated
  4. concentrationagain concentrated
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-053da04254f04ef39d0d968de781d37c
Source dataset
uspto-grants-2015_06
Patent number
US09067931B2

Reaction notes

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