Pyridine → 4-(2-Methyl-3-(4-methylbenzamido)phenyl)-6-morpholino-9H-pyrido[3,4-b]indole-1-carboxamide

HRID 2361349Notes

Reaction equation

HRID 2361349 reaction equation
[NH2:1][C:2]1[C:3]([CH3:30])=[C:4]([C:8]2[C:20]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([N:21]5[CH2:26][CH2:25][O:24][CH2:23][CH2:22]5)[CH:18]=4)[NH:13][C:12]=3[C:11]([C:27]([NH2:29])=[O:28])=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1.N1C=CC=CC=1>ClCCl>[CH3:30][C:3]1[C:2]([NH:1][C:36](=[O:37])[C:35]2[CH:39]=[CH:40][C:32]([CH3:31])=[CH:33][CH:34]=2)=[CH:7][CH:6]=[CH:5][C:4]=1[C:8]1[C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)[CH:18]=3)[NH:13][C:12]=2[C:11]([C:27]([NH2:29])=[O:28])=[N:10][CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 134054-Methylbenzoyl ChlorideHCID 679946124-(3-Amino-2-methylphenyl)-6-morpholino-9H-pyrido[3,4-b]indole-1-carboxamide

Product 1

HCID 547667144-(2-Methyl-3-(4-methylbenzamido)phenyl)-6-morpholino-9H-pyrido[3,4-b]indole-1-carboxamideYield 52.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-(3-amino-2-methylphenyl)-6-morpholino-9H-pyrido[3,4-b]indole-1-carboxamide (0.0287 g, 0.071 mmol) and 4-methylbenzoyl chloride (0.013 g, 0.086 mmol) in dichloromethane (0.953 mL) under nitrogen was added pyridine (0.012 mL, 0.143 mmol). The vial was sealed and stirred at 40° C. After 15 min, the reaction was cooled to room temperature and concentrated in vacuo. It was diluted with MeOH (1 mL) and purified by reverse phase HPLC. The appropriate fractions were combined, basified with NaHCO3 (solid), and concentrated in vacuo. It was extracted with CH2Cl2 (3×). The organic layers were combined, dried over Na2SO4, and concentrated in vacuo to give the desired product (0.0192 g, 0.037 mmol, 51.7% yield) as a light yellow solid. LC/MS (M+H)=520.25; 1H NMR (400 MHz, DMSO-d6) δ ppm 11.56 (s, 1H), 10.00 (s, 1H), 8.31 (d, J=2.2 Hz, 1H), 8.15 (s, 1H), 7.92 (s, 1H), 7.90 (s, 1H), 7.75 (d, J=2.0 Hz, 1H), 7.70 (d, J=8.80 Hz, 1H), 7.55 (d, J=7.0 Hz, 1H), 7.45 (t, J=7.7 Hz, 1H), 7.35 (s, 1H), 7.33 (s, 1H), 7.25-7.32 (m, 1H), 6.53 (d, J=2.2 Hz, 1H), 3.68 (m, 4H), 2.80-2.91 (m, 4H), 2.38 (s, 3H), 1.94 (s, 3H).

Workup

  1. customThe vial was sealed
  2. temperaturethe reaction was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. additionIt was diluted with MeOH (1 mL)
  5. custompurified by reverse phase HPLC
  6. concentrationconcentrated in vacuo
  7. extractionIt was extracted with CH2Cl2 (3×)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-84de7d29f87e4b498998d2e5ac3a2a30
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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