Dimethylamine → HCID 11341075, compound

HRID 383981Notes

Reaction equation

HRID 383981 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=O.[S:13]1[C:17]2[CH:18]=[CH:19][C:20]([CH:22]([N:33]3[C@H:38]([CH2:39][CH:40]([CH3:42])[CH3:41])[C:37](=[O:43])[NH:36][C@H:35]([CH:44]4[CH2:52][C:51]5[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=5)[CH2:45]4)[C:34]3=[O:53])[C:23]([NH:25][C:26]3C=CC=CC=3O)=[O:24])=[CH:21][C:16]=2[CH:15]=[CH:14]1.CNC.O1CCCC1>ClCCl>[S:13]1[C:17]2[CH:18]=[CH:19][C:20]([C@@H:22]([N:33]3[C@H:38]([CH2:39][CH:40]([CH3:41])[CH3:42])[C:37](=[O:43])[NH:36][C@H:35]([CH:44]4[CH2:52][C:51]5[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=5)[CH2:45]4)[C:34]3=[O:53])[C:23]([N:25]([CH3:26])[CH3:1])=[O:24])=[CH:21][C:16]=2[CH:15]=[CH:14]1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 68847229HCID 68847229, compound

Product 1

HCID 11341075HCID 11341075, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Carbonyldiimidazole (100 mg) was suspended in anhydrous dichloromethane (1 mL) and the suspension was left at room temperature for 15 minutes. 2RS)-2-(1-benzothien-5-yl)-2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-isobutyl-2,5-dioxopiperazin-1-yl]-N-(2-hydroxyphenyl)ethanamide (200 mg) was then added and the mixture was stirred at room temperature for 5 hours 20 minutes. The resulting brown solution was then treated with a 2.0M solution of dimethylamine in tetrahydrofuran (1.0 mL, 6 equiv.) and the resulting mixture was stirred for 30 minutes and then left to stand at room temperature for 18 hours 15 minutes. The reaction mixture was evaporated under reduced pressure. The crude product was purified by silica column chromatography eluting with 1:1 v/v ethyl acetate:cyclohexane. The required fractions were combined and evaporated in vacuo to give (2R)-2-(benzothien-5-yl)-2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-isobutyl-2,5-dioxopiperazin-1-yl]-N,N-dimethylethanamide as a white solid (90 mg).

Workup

  1. stirringthe resulting mixture was stirred for 30 minutes
  2. waitleft
  3. waitto stand at room temperature for 18 hours 15 minutes
  4. customThe reaction mixture was evaporated under reduced pressure
  5. customThe crude product was purified by silica column chromatography
  6. washeluting with 1:1 v/v ethyl acetate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-47bcd1e3b87e4ec7a5a08d4d0c62f21c
Source dataset
uspto-grants-2013_02
Patent number
US08367673B2

Reaction notes

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