HCID 23498818, compound → HCID 44299338, compound

HRID 1836156Notes

Reaction equation

HRID 1836156 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][C:13]2[C:21]3[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=3[NH:15][C:14]=2[CH:22]=O)[CH2:6][CH2:5]1.OC1CCN(CCCC2C3CCCCC=3NC=2C=O)CC1.[CH2:45]([S:47]([C:50]1[CH:51]=[C:52]2[C:56](=[CH:57][CH:58]=1)[NH:55][C:54](=[O:59])[CH2:53]2)(=[O:49])=[O:48])[CH3:46]>>[CH2:45]([S:47]([C:50]1[CH:51]=[C:52]2[C:56](=[CH:57][CH:58]=1)[NH:55][C:54](=[O:59])/[C:53]/2=[CH:22]\[C:14]1[NH:15][C:16]2[CH2:17][CH2:18][CH2:19][CH2:20][C:21]=2[C:13]=1[CH2:12][CH2:11][CH2:10][N:7]1[CH2:6][CH2:5][N:4]([CH2:3][CH2:2][OH:1])[CH2:9][CH2:8]1)(=[O:48])=[O:49])[CH3:46]

Participants

4

Reactant 3

HCID 23498818HCID 23498818, compoundHCID 23498820HCID 23498820, compoundHCID 23498854HCID 23498854, compound

Product 1

HCID 44299338HCID 44299338, compoundYield 59.8%

Procedure

3-{3-[4-(2-Hydroxy-ethyl)-piperazin-1-yl]- propyl}-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde (64 mg, 0.2 mmol), prepared by following the procedure described for 3-[3-(4-hydroxy-piperidin-1-yl)- propyl]-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde (example 20), was condensed with 5-ethylsulfonyloxindole (Example 5) (69 mg, 0.2 mmol, 65%pure). The reaction solution was purified by flash chromatography, eluting with dichloromethane/methanol (20/1, 15/1 then 10/1) to provide 63 mg of the desired compound.

Workup

  1. customThe reaction solution was purified by flash chromatography
  2. washeluting with dichloromethane/methanol (20/1, 15/1

Sources & evidence

ORD record
ord-d74d997128754cb4936a1c553d7841d6
Source dataset
uspto-grants-2004_08
Patent number
US06777417B2

Reaction notes

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