Ammonia → HCID 68283864, compound

HRID 1469586Notes

Reaction equation

HRID 1469586 reaction equation
[CH3:1][N:2]1[CH2:25][CH2:24][C:5]2[N:6]([CH2:14][C:15]3([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[CH2:17][O:16]3)[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[NH3:26]>CO>[NH2:26][CH2:17][C:15]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)([OH:16])[CH2:14][N:6]1[C:7]2[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=2[C:4]2[CH2:3][N:2]([CH3:1])[CH2:25][CH2:24][C:5]1=2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86677153HCID 86677153, compound

Product 1

HCID 68283864HCID 68283864, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,8-Dimethyl-5-((2-(pyridin-3-yl)oxiran-2-yl)methyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (100 mg, 0.3 mmol) was dissolved in MeOH (2 mL) and aq. ammonia (2 mL) and the reaction mixture was allowed to stir at RT for 24 h. The progress of reaction was monitored by LCMS. The volatiles were removed under reduced pressure to obtain a crude oily product that was purified by reverse phase HPLC to afford 7 mg of 1-amino-3-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-2-(pyridin-3-yl)propan-2-ol as TFA salt. 1H NMR (CD3OD, TFA salt) δ (ppm): 8.65 (m, 2H), 8.43 (dd, 1H), 7.75 (m, 1H), 7.18 (d, 1H), 6.88 (m, 2H), 4.67 (d, 1H), 4.55 (m, 2H), 4.29 (t, 1H), 3.90 (m, 2H), 3.69 (m, 1H), 3.5 (m, 2H), 3.1 (m, 1H), 3.11 (s, 3H), 2.34 (s, 3H). Separation by chiral HPLC provides enantiomers II-264a-b.

Workup

  1. customThe progress of reaction
  2. customThe volatiles were removed under reduced pressure
  3. customto obtain a crude oily product that
  4. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-dcecf21d8f2740659430f3799e9d811a
Source dataset
uspto-grants-2015_04
Patent number
US09006263B2

Reaction notes

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