(S)-2-(2-Methoxyethyl)piperazine → HCID 135525321, compound

HRID 131515Notes

Reaction equation

HRID 131515 reaction equation
Cl.[CH:2]1[C:7]2[S:8][C:9]3[NH:10][C:11]4[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=4[N:13]=[C:14]([NH2:16])[C:15]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:21][O:22][CH2:23][CH2:24][C@H:25]1[CH2:30]N[CH2:28][CH2:27][NH:26]1>>[CH3:21][O:22][CH2:23][CH2:24][C@@H:25]1[NH:26][CH2:27][CH2:28][N:16]([C:14]2[C:15]3[C:6]4[CH:5]=[CH:4][CH:3]=[CH:2][C:7]=4[S:8][C:9]=3[NH:10][C:11]3[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=3[N:13]=2)[CH2:30]1

Participants

3

Reactant 2

HCID 55287560(S)-2-(2-Methoxyethyl)piperazineHCID 135797727HCID 135797727, compound

Product 1

HCID 135525321HCID 135525321, compoundYield 14.7%

Conditions

Temperature
115 °C

Procedure

Following the method of Example 380, using 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 (0.38 g, 2.7 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 them 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 (0.075 g). Mass spectrum (APCI+, m/e): 393 (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 them 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-007ed32613e34af89b0cb7111133fd76
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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