Acetic Anhydride → HCID 89793631, compound

HRID 1055892Notes

Reaction equation

HRID 1055892 reaction equation
[CH3:1][C:2]1[C:11]([NH:12][C@H:13]2[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:18]2[NH:26][C:25]3[CH2:24][CH2:23][NH:22][C:21](=[O:27])[C:20]=3[CH:19]=2)[N:3]=1.[CH3:28][C:29](OC(C)=O)=[O:30]>C(Cl)Cl>[C:29]([N:15]1[CH2:16][CH2:17][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:18]2[NH:26][C:25]4[CH2:24][CH2:23][NH:22][C:21](=[O:27])[C:20]=4[CH:19]=2)[CH:7]=[CH:6][CH:5]=3)[CH2:14]1)(=[O:30])[CH3:28]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 89783366HCID 89783366, compound

Product 1

HCID 89793631HCID 89793631, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Prepared according to Example 50, using TEA (57.6 μl, 0.414 mmol), (S)-2-(2-methyl-3-(pyrrolidin-3-ylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Ex. 55, 125 mg, 0.345 mmol), Ac2O (65.1 μl, 0.690 mmol), and DCM (3.5 mL) stirring at 25° C. for 1.5 h. Purification by trituration with Et2O and elution through a Si-carbonate cartridge (Silicycle) provided (S)-2-(3-((1-acetylpyrrolidin-3-yl)amino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (23 mg, 16.5%). 1H NMR (DMSO-d6) δ: 7.84-7.90 (m, 1H), 7.53-7.59 (m, 1H), 7.32-7.40 (m, 1H), 7.13-7.21 (m, 2H), 6.89-6.97 (m, 1H), 4.61-4.75 (m, 1H), 3.45-3.98 (m, 3H), 3.38-3.45 (m, 1H), 2.82-2.90 (m, 2H), 2.57 (s, 3H), 2.04-2.44 (m, 2H), 1.98 (s, 3H), 1.12-1.21 (m, 2H). m/z (ESI, +ve) 405.1 (M+H)+.

Workup

  1. customPrepared
  2. customPurification by trituration
  3. washwith Et2O and elution through a Si-carbonate cartridge (Silicycle)

Sources & evidence

ORD record
ord-91df1414cc4048e2b5e1cfb736601f2c
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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