Dimethylamine → HCID 68283791, compound

HRID 2408671Notes

Reaction equation

HRID 2408671 reaction equation
Cl[C:2]([C:22]1[CH:27]=[N:26][CH:25]=[CH:24][N:23]=1)([CH3:21])[CH2:3][N:4]1[C:16]2[CH2:15][CH2:14][N:13]3[CH2:17][CH2:18][CH2:19][CH:12]3[C:11]=2[C:10]2[CH:9]=[C:8]([CH3:20])[CH:7]=[CH:6][C:5]1=2.[CH3:28][NH:29][CH3:30]>O>[CH3:28][N:29]([CH3:30])[C:2]([CH3:21])([C:22]1[CH:27]=[N:26][CH:25]=[CH:24][N:23]=1)[CH2:3][N:4]1[C:16]2[CH2:15][CH2:14][N:13]3[CH2:17][CH2:18][CH2:19][CH:12]3[C:11]=2[C:10]2[CH:9]=[C:8]([CH3:20])[CH:7]=[CH:6][C:5]1=2

Participants

4

Reactant 2

HCID 674DimethylamineHCID 68283522HCID 68283522, compound

Product 1

HCID 68283791HCID 68283791, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-(2-Chloro-2-pyrazin-2-yl-propyl)-9-methyl-2,3,4,5,6,10c-hexahydro-1H-3a,6-diaza-cyclopenta[c]fluorene (500 mg, 1.31 mmol) in 40% dimethylamine in water (30 mL) was heated at 100° C. for 3 h. The reaction mixture was cooled at RT and extracted with EtOAc (3×50 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated to obtain the crude product, which was purified by reverse phase chromatography to obtain 62 mg of dimethyl-[1-methyl-2-(9-methyl-1,2,3,4,5,10c-hexahydro-3a,6-diaza-cyclopenta[c]fluoren-6-yl)-1-pyrazin-2-yl-ethyl]-amine. 1H NMR (CD3OD, TFA salt): δ (ppm): 8.06 (s, 1H), 7.48 (s, 1H), 7.21 (s, 1H), 7.17 (d, 1H), 7.00 (d, 1H), 4.98 (t, 1H), 4.28 (d, 2H), 3.6 (m, 3H), 3.39 (m, 2H), 3.2 (m, 1H), 3.15 (s, 6H), 2.8 (m, 1H), 2.7 (m, 1H), 2.39 (s, 3H), 2.17 (m, 3H). Chiral HPLC separated the racemate into diastereomers II-6a-d.

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customto obtain the crude product, which
  5. customwas purified by reverse phase chromatography

Sources & evidence

ORD record
ord-35fb81689f5b44389dcd1f0990222933
Source dataset
uspto-grants-2014_08
Patent number
US08815843B2

Reaction notes

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