2,2-Dimethylpyrrolidine → HCID 89783509, compound

HRID 1056038Notes

Reaction equation

HRID 1056038 reaction equation
F[C:2]1[CH:3]=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([C:12]1[NH:20][C:19]3[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=3[CH:13]=1)[CH:8]=[CH:7][CH:6]=2.[CH3:22][C:23]1(C)C[CH2:26][CH2:25][NH:24]1>>[CH2:23]([N:24]([CH2:25][CH3:26])[C:2]1[CH:3]=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([C:12]1[NH:20][C:19]3[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=3[CH:13]=1)[CH:8]=[CH:7][CH:6]=2)[CH3:22]

Participants

3

Reactant 2

HCID 4147732,2-DimethylpyrrolidineHCID 897843702-(3-fluoroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 89783509HCID 89783509, compoundYield 50%

Conditions

Temperature
100 °C

Procedure

Prepared similarly to that described in Example 210 using 2-(3-fluoroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 210i; 82 mg, 0.290 mmol) and 2,2-dimethylpyrrolidine (57.6 mg, 0.581 mmol; ChemBridge, San Diego, Calif.) and heating at 100° C. for 16 h. Purification by rpHPLC (Phenomenex Gemini C18, 10 μm, 150×30 mm; 10-100% ACN/water with 0.1% TFA) provided 2-(3-(diethylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (50% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.61 (s, 6H) 1.96-2.06 (m, 4H) 2.87 (t, J=6.94 Hz, 2H) 3.43 (td, J=6.85, 2.35 Hz, 2H) 3.78 (t, J=6.16 Hz, 2H) 6.95 (br. s., 1H) 7.07 (d, J=2.15 Hz, 1H) 7.36 (t, J=7.73 Hz, 1H) 7.66 (dd, J=8.02, 1.17 Hz, 1H) 7.89-7.94 (m, 1H) 8.62 (s, 1H) 11.99 (br. s., 1H). MS (ESI, pos. ion) m/z: 362.1 (M+1).

Workup

  1. customPrepared similarly to that
  2. customPurification by rpHPLC (Phenomenex Gemini C18, 10 μm, 150×30 mm; 10-100% ACN/water with 0.1% TFA)

Sources & evidence

ORD record
ord-4bdeb08c04584a05bf32d1fc26080644
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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