Acetic Anhydride → HCID 59454890, compound

HRID 1400580Notes

Reaction equation

HRID 1400580 reaction equation
[CH3:1][NH:2][C:3]1[CH:11]=[CH:10][C:9]2[N:8]([CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[CH3:14])[C:7]3[CH2:21][CH2:22][N:23]([CH3:25])[CH2:24][C:6]=3[C:5]=2[CH:4]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27].[OH-].[Na+]>>[CH3:1][N:2]([C:3]1[CH:11]=[CH:10][C:9]2[N:8](/[CH:12]=[C:13](/[C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)\[CH3:14])[C:7]3[CH2:21][CH2:22][N:23]([CH3:25])[CH2:24][C:6]=3[C:5]=2[CH:4]=1)[C:26](=[O:28])[CH3:27]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 68484435HCID 68484435, compound

Product 1

HCID 59454890HCID 59454890, compound

Procedure

2,3,4,5-Tetrahydro-N,2-dimethyl-5-(2-(pyridin-4-yl)prop-1-enyl)-1H-pyrido[4,3-b]indol-8-amine (23 mg) was charged in round bottom flask and acetic anhydride (0.7 mL) was added. The contents were stirred at RT for 30 min. The reaction mixture was basified with 1N NaOH and compound extracted with EtOAc (2×25 mL). The organic layer was concentrated under vacuum and recrystallized in DCM:Hexane (1:3) to yield 2.38 mg of desired compound. 1H NMR (CDCl3, free base) δ (ppm): 8.62 (d, 2H), 7.42 (d, 2H), 7.25 (s, 1H), 7.10 (dd, 2H), 6.98 (d, 1H), 3.70 (s, 2H), 3.30 (s, 3H), 2.82 (m, 4H), 3.60 (s, 3H), 2.04 (s, 3H), 1.90 (s, 3H).

Workup

  1. extractionextracted with EtOAc (2×25 mL)
  2. concentrationThe organic layer was concentrated under vacuum
  3. customrecrystallized in DCM:Hexane (1:3)

Sources & evidence

ORD record
ord-0a1857e0e75b4d8d91a562b0ab37dacf
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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