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

HRID 1056068Notes

Reaction equation

HRID 1056068 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([O-])(O)=O.[Na+]>CO.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

6

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 897936472-(2-methyl-3-((3R)-3-piperidinylamino)-5-quinoxalinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one

Product 1

HCID 897937322-(3-(((3R)-1-acetyl-3-piperidinyl)amino)-2-methyl-5-quinoxalinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-oneYield 34%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
25 °C

Procedure

Prepared according to Example 50, using TEA (39.9 μl, 0.287 mmol), 2-(2-methyl-3-((3R)-3-piperidinylamino)-5-quinoxalinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (Ex. 75, 90 mg, 0.239 mmol), Ac2O (45.1 μl, 0.478 mmol), and DCM (2.4 mL) and stirring at 25° C. for 1 h. Isolation of the free base from the mixture by addition of saturated aq. NaHCO3 and extraction with 10% MeOH/DCM, followed by drying of the organic extract over Na2SO4, filtration, and concentration under reduced pressure afforded 2-(3-(((3R)-1-acetyl-3-piperidinyl)amino)-2-methyl-5-quinoxalinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (34 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), 2.07 (s, 3H), 1.59 (s, 3H), 1.10-1.22 (m, 3H). m/z (ESI, +ve) 419.1 (M+H)+.

Workup

  1. customPrepared
  2. customby drying of the
  3. extractionorganic extract over Na2SO4, filtration, and concentration under reduced pressure

Sources & evidence

ORD record
ord-6341d41fcf8d41da98afdbbcdd15789d
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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