Isopropanol → HCID 44159219, compound

HRID 517870Notes

Reaction equation

HRID 517870 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]3[CH2:17][CH2:18][N:19]([CH3:21])[CH2:20][C:5]=3[C:4]=2[CH:3]=1.[CH3:22]C(O)C>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][C:12]([O:14][CH:15]([CH3:22])[CH3:16])=[O:13])[C:6]3[CH2:17][CH2:18][N:19]([CH3:21])[CH2:20][C:5]=3[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 3776IsopropanolHCID 44159218Ethyl 2-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)acetate

Product 1

HCID 44159219HCID 44159219, compoundYield 10%

Procedure

Ethyl 2-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)acetate (100 mg, 0.32 mmol) was added to propan-2-ol (1.0 ml, excess) and the reaction mixture was heated at 100 deg C for 14 h. After completion of the reaction (monitored by LCMS) reaction mixture was concentrated and basified with aqueous saturated sodium bicarbonate, extracted with ethyl acetate. The organic layer was concentrated to dryness and the crude obtained was purified by silica gel chromatography (Eluent: 10% MeOH in dichloromethane) to get 10 mg (yield: 10%) of isopropyl 2-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)acetate. The free base product (10 mg, 0.03 mmol) was dissolved in THF (1.0 ml), oxalic acid (4 mg, 0.03 mmol) in THF (1.0 ml) was added slowly, the mixture was stirred at RT for 20 minutes and the solid obtained was filtered, washed with ether and dried to get 10 mg (yield: 83%) of isopropyl 2-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)acetate as oxalate salt. 1H NMR (DMSO) OXALATE SALT 7.60 (s, 1H), 7.50 (d, 1H), 7.20 (d, 1H), 5.1 (s, 2H), 4.90 (m, 1H), 4.50 (m, 1H), 4.20 (m, 1H), 3.5 (m, 2H), 3.10 (bs, 2H), 3.0 (s, 3H), 1.10 (d, 6H).

Workup

  1. temperaturethe reaction mixture was heated at 100 deg C for 14 h
  2. customAfter completion of the reaction (monitored by LCMS) reaction mixture
  3. concentrationwas concentrated
  4. extractionextracted with ethyl acetate
  5. concentrationThe organic layer was concentrated to dryness
  6. customthe crude obtained
  7. customwas purified by silica gel chromatography (Eluent: 10% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-ef14a21ed886426890d73b15105983c2
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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