Acetic Anhydride → HCID 59455198, compound

HRID 1400583Notes

Reaction equation

HRID 1400583 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:26])=[CH:9][N:10]2[C:18]3[CH:17]=[CH:16][C:15]([NH:19][CH3:20])=[CH:14][C:13]=3[C:12]3[CH2:21][N:22]([CH3:25])[CH2:23][CH2:24][C:11]2=3)=[CH:4][CH:3]=1.C(O[C:31](=[O:33])[CH3:32])(=O)C.[OH-].[Na+]>>[F:1][C:2]1[CH:3]=[CH:4][C:5](/[C:8](/[CH3:26])=[CH:9]/[N:10]2[C:18]3[CH:17]=[CH:16][C:15]([N:19]([CH3:20])[C:31](=[O:33])[CH3:32])=[CH:14][C:13]=3[C:12]3[CH2:21][N:22]([CH3:25])[CH2:23][CH2:24][C:11]2=3)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 68487455HCID 68487455, compound

Product 1

HCID 59455198HCID 59455198, compound

Procedure

5-(2-(4-Fluorophenyl)prop-1-enyl)-2,3,4,5-tetrahydro-N,2-dimethyl-1H-pyrido[4,3-b]indol-8-amine (30 mg) was charged in a round bottom flask. Acetic anhydride (0.5 mL) was added and the contents stirred at RT for 30 min. The reaction mixture was then basified with 1N NaOH and extracted with EtOAc (2×25 mL). The organic layer was concentrated under vacuum and purified through reverse phase column chromatography to yield 19.38 mg of the desired compound. 1H NMR (CD3OD, TFA salt) δ (ppm): 7.70 (m, 2H), 7.50 (s, 1H), 7.36 (d, 1H), 7.18 (m, 3H), 7.0 (s, 1H), 4.78 (d, 1H), 4.41 (d, 1H), 3.90 (m, 1H), 3.62 (m, 1H), 3.28 (s, 3H), 3.20 (m, 2H), 3.10 (s, 3H), 1.96 (s, 3H), 1.82 (s, 3H).

Workup

  1. extractionextracted with EtOAc (2×25 mL)
  2. concentrationThe organic layer was concentrated under vacuum
  3. custompurified through reverse phase column chromatography

Sources & evidence

ORD record
ord-90006b1164694e0a881511714b49d792
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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