Water → HCID 67313923, compound

HRID 1012848Notes

Reaction equation

HRID 1012848 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-a0d5a3ee32dd460d98c0fc51c31136c4
Source dataset
uspto-grants-2011_07
Patent number
US07977485B2

Reaction notes

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