Dimethylamine → HCID 68284338, compound

HRID 2408672Notes

Reaction equation

HRID 2408672 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:12]2[N:11]([CH2:15][CH:16](OS(C)(=O)=O)[C:17]3[CH:22]=[N:21][CH:20]=[CH:19][N:18]=3)[C:10]3[CH2:9][CH2:8][N:7]4[CH2:28][CH2:29][CH2:30][CH:6]4[C:5]=3[C:4]=2[CH:3]=1.[CH3:31][NH:32][CH3:33]>O>[CH3:31][N:32]([CH3:33])[CH:16]([C:17]1[CH:22]=[N:21][CH:20]=[CH:19][N:18]=1)[CH2:15][N:11]1[C:10]2[CH2:9][CH2:8][N:7]3[CH2:28][CH2:29][CH2:30][CH:6]3[C:5]=2[C:4]2[CH:3]=[C:2]([CH3:1])[CH:14]=[CH:13][C:12]1=2

Participants

4

Reactant 2

HCID 674DimethylamineHCID 86677144HCID 86677144, compound

Product 1

HCID 68284338HCID 68284338, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methanesulfonic acid 2-(9-methyl-1,2,3,4,5,10c-hexahydro-3a,6-diaza-cyclopenta[c]fluoren-6-yl)-1-pyrazin-2-yl-ethyl ester (300 mg, 0.70 mmol) in 40% dimethylamine in water (20 mL) was heated at 90° C. for 1 h. The reaction mixture was cooled to RT and extracted with DCM (12×50 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 60 mg of dimethyl-[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): 8.1 (s, 1H), 7.4 (s, 1H), 7.1 (d, 1H), 5.1 (t, 1H), 4.42 (m, 2H), 3.6 (m, 3H), 3.2 (m, 1H), 3.17 (m, 1H), 3.15 (s, 6H), 2.85 (m, 2H), 2.63 (m, 1H), 2.42 (s, 3H), 2.3 (m, 2H), 2.15 (m, 1H). Chiral HPLC separates the racemate into diastereomers II-7a-d.

Workup

  1. extractionextracted with DCM (12×50 mL) The combined organic layer
  2. dry with materialwas 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-4f28824420f14b798456dbe01b4f1c36
Source dataset
uspto-grants-2014_08
Patent number
US08815843B2

Reaction notes

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