Sodium Iodide → HCID 24884474, compound

HRID 1441268Notes

Reaction equation

HRID 1441268 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[CH:8]=[C:7]2[C:18]1[N:22]=[C:21]([CH2:23][N:24]2[CH2:29][CH2:28][NH:27][C@H:26]([CH2:30][OH:31])[CH2:25]2)[O:20][N:19]=1.[CH3:32][NH:33][C:34](=[O:37])[CH2:35]Cl.C(N(CC)C(C)C)(C)C.[I-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)[CH:8]=[C:7]2[C:18]1[N:22]=[C:21]([CH2:23][N:24]2[CH2:29][CH2:28][N:27]([CH2:35][C:34](=[O:37])[NH:33][CH3:32])[C@H:26]([CH2:30][OH:31])[CH2:25]2)[O:20][N:19]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 667732-chloro-N-methylacetamideHCID 81531DiisopropylethylamineHCID 68540091HCID 68540091, compound

Product 1

HCID 24884474HCID 24884474, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (S)-7-chloro-3-[5-(3-hydroxymethylpiperazin-1-ylmethyl)-[1,2,4]-oxadiazol-3-yl]-1-[(tetrahydropyran-4-yl)methyl]-1H-indole (22 mg, 0.049 mmol), N-methyl-2-chloroacetamide (11 mg, 0.098 mmol), N,N-diisopropylethylamine (19 mg, 0.15 mmol) and sodium iodide (7 mg, 0.049 mmol) in dimethylformamide (2.0 ml) was subjected to microwave irradiation at 160° C. for 5 minutes. The mixture was filtered through a 5 g Strata™ SCX giga tube, eluting with dichloromethane, methanol and then 2 M ammonia in methanol, and purified by flash column chromatography eluting with ethyl acetate to 33% (v/v) methanol in ethyl acetate to afford the title compound (23.9 mg, 0.046 mmol). EsIMS: m/z 539.8, 517.5 [M+H]+, 503.1, 200.6.

Workup

  1. customirradiation at 160° C. for 5 minutes
  2. filtrationThe mixture was filtered through a 5 g Strata™ SCX giga tube
  3. washeluting with dichloromethane, methanol
  4. custom2 M ammonia in methanol, and purified by flash column chromatography
  5. washeluting with ethyl acetate to 33% (v/v) methanol in ethyl acetate

Sources & evidence

ORD record
ord-7ae1f8c9083a496ca2ab70dbcb7746de
Source dataset
uspto-grants-2010_02
Patent number
US07655645B2

Reaction notes

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