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

HRID 1055891Notes

Reaction equation

HRID 1055891 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.CCN(CC)CC.[CH3:35][C:36](OC(C)=O)=[O:37]>C(Cl)Cl>[C:36]([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:37])[CH3:35]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 89793617(R)-2-(2-methyl-3-(pyrrolidin-3-ylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 1185119342-(3-(((3R)-1-acetyl-3-pyrrolidinyl)amino)-2-methyl-5-quinoxalinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-oneYield 47.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared according to Example 50, using (R)-2-(2-methyl-3-(pyrrolidin-3-ylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Ex. 61, 135 mg, 0.372 mmol), Et3N (57.0 μl, 0.410 mmol), and Ac2O (70.3 μl, 0.745 mmol) in DCM (3.7 mL). Purification by trituration with Et2O provided 2-(3-(((3R)-1-acetyl-3-pyrrolidinyl)amino)-2-methyl-5-quinoxalinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (72 mg, 47.8%). 1H NMR (DMSO-d6) δ: 7.84-7.91 (m, 1H), 7.57-7.62 (m, 1H), 7.32-7.40 (m, 1H), 7.12-7.21 (m, 2H), 6.91-6.98 (m, 1H), 4.61-4.75 (m, 1H), 3.45-3.98 (m, 3H), 3.38-3.45 (m, 2H), 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 with Et2O

Sources & evidence

ORD record
ord-f71ed578dfed40c8a2c5d0094bb28579
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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