Ammonium Acetate → 4-[2-(4-Hydroxy-piperdin-1-yl)-2-oxo-ethyl]-6,6-dimethyl-morpholine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amide

HRID 552249Notes

Reaction equation

HRID 552249 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:15][C:16]([CH:18]3[N:23]([CH2:24][C:25](O)=[O:26])[CH2:22][C:21]([CH3:29])([CH3:28])[O:20][CH2:19]3)=[O:17])[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1.ON1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.[C:37]([O-])(=[O:39])C.[NH4+]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:15][C:16]([CH:18]3[CH2:19][O:20][C:21]([CH3:28])([CH3:29])[CH2:22][N:23]3[CH2:24][C:25]([N:34]3[CH2:35][CH2:36][CH:37]([OH:39])[CH2:32][CH2:33]3)=[O:26])=[O:17])[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 12463393Piperazin-1-olHCID 59337527[5-(6-Chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholin-4-yl]-acetic acid

Product 1

HCID 671706094-[2-(4-Hydroxy-piperdin-1-yl)-2-oxo-ethyl]-6,6-dimethyl-morpholine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amideYield 31%

Procedure

The desired compound was synthesized using [5-(6-Chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholin-4-yl]-acetic acid and 4-hydroxypiperazine following Method F in 31% yield. 1H-NMR (300 MHz, D2O): δ 8.85 (1H,s), 8.19 (2H, s), 7.82 (1H, s), 7.44 (1H, s), 4.15 (2H, m), 3.9-3.75 (4H, m), 3.6 (2H, m), 3.56 (2H, m), 3.12 (1H, m), 2.9 (3H, m), 2.8 (1H, m), 1.7 (2H, m) 1.34 (3H, s), 1.19 (3H, s). Retention time (LC, method: ammonium acetate standard): 1.5 min

Workup

  1. custom1.5 min

Sources & evidence

ORD record
ord-eeaaa9207ee048758aa8320ecc3d937c
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

Loading…