Water → HCID 49779444, compound

HRID 1773281Notes

Reaction equation

HRID 1773281 reaction equation
[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[H-].[Na+].[CH3:18][C:19]1([C:22]2[CH:27]=[N:26][CH:25]=[CH:24][N:23]=2)[CH2:21][O:20]1.O>CN(C=O)C>[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[N:6]([CH2:18][C:19]([C:22]3[CH:27]=[N:26][CH:25]=[CH:24][N:23]=3)([OH:20])[CH3:21])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2092911H-Pyrido[4,3-b]indole, 2,3,4,5-tetrahydro-2,8-dimethyl-HCID 86665936HCID 86665936, compound

Product 1

HCID 49779444HCID 49779444, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido(4,3-b)indole (350 mg, 1.75 mmol) in DMF (4 mL) was added sodium hydride (210 mg, 5.25 mmol) followed by dropwise addition of 2-(2-methyl oxiranyl)pyrazine (310 mg, 2.275 mmol) at 10° C. and the reaction mixture was further stirred at RT for 16 h. After completion, the reaction mixture was poured into ice cooled water, extracted with EtOAc (3×75 mL). The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated yielding crude product, which was re-crystallized in ether and hexane to yield a yellow solid product (350 mg). 1H NMR (DMSO, Oxalate salt) d (ppm): 8.65 (s, 1H), 8.55 (s, 1H), 8.50 (d, 1H), 7.10 (s, 1H), 6.90 (d, 1H), 6.78 (d, 1H), 4.30 (m, 4H), 3.20 (m, 2H), 3.0 (m, 2H), 2.90 (s, 3H), 2.30 (s, 3H), 1.50 (s, 3H).

Workup

  1. additionAfter completion, the reaction mixture was poured into ice
  2. extractionextracted with EtOAc (3×75 mL)
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customyielding crude product, which
  7. customwas re-crystallized in ether

Sources & evidence

ORD record
ord-9c55bc36fb154d2f9e343525746a9a70
Source dataset
uspto-grants-2016_02
Patent number
US09255094B2

Reaction notes

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