Acetic Anhydride → 2-(3-(((3S)-1-acetyl-3-piperidinyl)amino)-2-methyl-5-quinoxalinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one

HRID 1056069Notes

Reaction equation

HRID 1056069 reaction equation
[CH3:1][C:2]1[C:11]([NH:12][C@H:13]2[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]2)=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:19]2[NH:27][C:26]3[CH2:25][CH2:24][NH:23][C:22](=[O:28])[C:21]=3[CH:20]=2)[N:3]=1.[CH3:29][C:30](OC(C)=O)=[O:31]>C(Cl)Cl>[C:30]([N:15]1[CH2:16][CH2:17][CH2:18][C@H:13]([NH:12][C:11]2[C:2]([CH3:1])=[N:3][C:4]3[C:9]([N:10]=2)=[C:8]([C:19]2[NH:27][C:26]4[CH2:25][CH2:24][NH:23][C:22](=[O:28])[C:21]=4[CH:20]=2)[CH:7]=[CH:6][CH:5]=3)[CH2:14]1)(=[O:31])[CH3:29]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 89783857(S)-2-(2-methyl-3-(piperidin-3-ylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 897936932-(3-(((3S)-1-acetyl-3-piperidinyl)amino)-2-methyl-5-quinoxalinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-oneYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Prepared according to Example 50, using TEA (37.7 μl, 0.271 mmol, Sigma Aldrich), (S)-2-(2-methyl-3-(piperidin-3-ylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Ex. 76, 85 mg, 0.226 mmol), Ac2O (42.6 μl, 0.452 mmol), and DCM (2.3 mL) and stirring at 25° C. for 1 h. Purification by concentration of the reaction solution, solubilization in MeOH, and filtration through a pre-washed column of Si-carbonate (SiliaPrep, Silicyle) provided 2-(3-(((3S)-1-acetyl-3-piperidinyl)amino)-2-methyl-5-quinoxalinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (28 mg, 30%). 1H NMR (DMSO-d6) δ: 7.85-7.91 (m, 1H), 7.77-7.83 (m, 1H), 7.54-7.63 (m, 2H), 7.30-7.40 (m, 2H), 7.05-7.11 (m, 1H), 4.45-4.55 (m, 1H), 4.27-4.39 (m, 1H), 4.13-4.27 (m, 1H), 3.96-4.10 (m, 1H), 3.86-3.95 (m, 1H), 3.76-3.86 (m, 1H), 3.39-3.46 (m, 3H), 2.87-2.97 (m, 1H), 2.01-2.07 (m, 3H), 1.59 (s, 3H), 1.10-1.22 (m, 3H). m/z (ESI, +ve) 419.1 (M+H)+.

Workup

  1. customPrepared
  2. customPurification by concentration of the reaction solution, solubilization in MeOH
  3. filtrationfiltration through a pre-washed column of Si-carbonate (SiliaPrep, Silicyle)

Sources & evidence

ORD record
ord-94756eca236343318986c5ab19bcc4cb
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

Loading…