(S)-2-(2-Methoxyethyl)piperazine → HCID 135464320, compound

HRID 131516Notes

Reaction equation

HRID 131516 reaction equation
Cl.[F:2][C:3]1[CH:21]=[CH:20][C:6]2[NH:7][C:8]3[S:9][C:10]4[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=4[C:12]=3[C:13]([NH2:15])=[N:14][C:5]=2[CH:4]=1.[CH3:22][O:23][CH2:24][CH2:25][C@H:26]1[CH2:31]N[CH2:29][CH2:28][NH:27]1>>[F:2][C:3]1[CH:21]=[CH:20][C:6]2[NH:7][C:8]3[S:9][C:10]4[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=4[C:12]=3[C:13]([N:15]3[CH2:29][CH2:28][NH:27][C@@H:26]([CH2:25][CH2:24][O:23][CH3:22])[CH2:31]3)=[N:14][C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 55287560(S)-2-(2-Methoxyethyl)piperazineHCID 136384186HCID 136384186, compound

Product 1

HCID 135464320HCID 135464320, compoundYield 18%

Conditions

Temperature
115 °C

Procedure

Following the method of Example 380 using 8-fluoro-11H-12-thia-6,11-diaza-dibenzo[a,f]azulen-5-ylamine hydrochloride (0.40 g, 1.3 mmol) and (S)-2-(2-methoxy-ethyl)-piperazine (0.36 g, 2.5 mmol), stirring at 115° C. for 24 hours, wash the separated organic layer with 0.1 N NaOH (2×), and extract the combined aqueous layers with ethyl acetate. Combine the organics and wash with a saturated solution of sodium chloride (3×), and then dry (sodium sulfate), filter, and concentrate under reduced pressure to a residue. Purify the residue by flash chromatography, eluting with a gradient of a solution of 5% 2M ammonia in methanol, in dichloromethane (in dichloromethane) to give the title compound (0.096 g). Mass spectrum (APCI+, m/e): 411 (M+1).

Workup

  1. washwash the separated organic layer with 0.1 N NaOH (2×)
  2. extractionextract the combined aqueous layers with ethyl acetate
  3. washwash with a saturated solution of sodium chloride (3×)
  4. dry with materialdry (sodium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure to a residue
  7. customPurify the residue by flash chromatography
  8. washeluting with a gradient of a solution of 5% 2M ammonia in methanol, in dichloromethane (in dichloromethane)

Sources & evidence

ORD record
ord-e5168557bd974ef3b553ae5ca2058bd5
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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