Diethyl Ether → HCID 10439569, compound

HRID 2357504Notes

Reaction equation

HRID 2357504 reaction equation
[CH3:1][N:2]([CH3:35])[C:3]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([N:13]2[CH2:18][CH:17]=[C:16]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([Cl:28])[CH:26]=4)[NH:21][CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[CH2:5][CH2:4]1.Cl[Si](C)(C)C.C(OCC)C>CC(CC)=O>[ClH:28].[CH3:1][N:2]([CH3:35])[C:3]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:4][CH2:5][CH:6]([CH2:9][NH:10][C:11]([N:13]2[CH2:14][CH:15]=[C:16]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([Cl:28])[CH:26]=4)[NH:21][CH:20]=3)[CH2:17][CH2:18]2)=[O:12])[CH2:7][CH2:8]1.[CH3:1][N:2]([CH3:35])[C:3]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:4][CH2:5][CH:6]([CH2:9][NH:10][C:11]([N:13]2[CH2:14][CH:15]=[C:16]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([Cl:28])[CH:26]=4)[NH:21][CH:20]=3)[CH2:17][CH2:18]2)=[O:12])[CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 6397ChlorotrimethylsilaneHCID 10439569HCID 10439569, compound

Product 2

HCID 10439569HCID 10439569, compoundYield 252.9%HCID 67531970HCID 67531970, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The polar diastereoisomer of 4-(5-chloro-1H-indol-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide (246 mg, 0.5 mmole) was dissolved in ethyl methyl ketone (10 ml). Chlorotrimethylsilane (95 μl, 0.75 mmole) was added dropwise at RT while stirring. After stirring for 1 hour a small amount of precipitate had formed. Diethyl ether (35 ml) was added to the reaction solution. The reaction solution was then stirred vigorously for 2 hours at RT. An orange precipitate formed. The solid was filtered off under suction, washed with diethyl ether (3×2 ml) and dried in vacuo. The hydrochloride of the polar diastereoisomer of 4-(5-chloro-1H-indol-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide (207 mg, m.p. 183°-185° C., 78%) was thereby obtained as a cinnamon-coloured solid (Example 59).

Workup

  1. stirringAfter stirring for 1 hour a small amount of precipitate
  2. customhad formed
  3. stirringThe reaction solution was then stirred vigorously for 2 hours at RT
  4. customAn orange precipitate formed
  5. filtrationThe solid was filtered off under suction
  6. washwashed with diethyl ether (3×2 ml)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-8251c9fd65a14c66a41d1f269c663f40
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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