Methylamine → HCID 68283926, compound

HRID 1469464Notes

Reaction equation

HRID 1469464 reaction equation
CS(O[CH:6]([C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)[CH2:7][N:8]1[C:16]2[CH:15]=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=2[C:10]2[CH2:18][N:19]([CH3:22])[CH2:20][CH2:21][C:9]1=2)(=O)=O.[CH3:29][NH2:30]>>[CH3:22][N:19]1[CH2:20][CH2:21][C:9]2[N:8]([CH2:7][CH:6]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[NH:30][CH3:29])[C:16]3[CH:15]=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=3[C:10]=2[CH2:18]1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 86677141HCID 86677141, compound

Product 1

HCID 68283926HCID 68283926, compound

Procedure

A solution of 2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)-1-(pyridin-4-yl)ethyl methanesulfonate (250 mg, 0.62 mmol) in methyl amine (3 mL, 40% in water) was stirred at 90° C. for 12 h. The progress of reaction was monitored by LCMS. The reaction mixture was extracted with EtOAc. The organic layer was dried and concentrated to get the crude product, which was purified by reverse phase HPLC to obtain the 2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)-N-methyl-1-(pyridin-4-yl)ethanamine. 1H NMR (CDCl3, freebase): δ (ppm): 8.59 d (2H), 7.3 d (2H), 7.29 d (1H), 7.23 s (1H), 7.03 d (1H), 4.19 m (1H), 4.03 m (2H), 3.66 dd (2H), 2.8 m (3H), 2.6 m (1H), 2.55 s (3H), 2.47 s (3H), 2.18 s (3H). Chiral HPLC provided enantiomers 151a and 151b.

Workup

  1. customThe progress of reaction
  2. extractionThe reaction mixture was extracted with EtOAc
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customto get the crude product, which
  6. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-e83dde3e1af542748eae01455508f489
Source dataset
uspto-grants-2015_04
Patent number
US09006263B2

Reaction notes

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