2,2-diMethylazetidine → HCID 89783888, compound

HRID 1056045Notes

Reaction equation

HRID 1056045 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([CH3:27])[CH2:26][CH2:25][NH:24]1>>[CH3:22][C:23]1([CH3:27])[CH2:26][CH2:25][N:24]1[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

Participants

3

Reactant 2

HCID 251591902,2-diMethylazetidineHCID 897843702-(3-fluoroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 89783888HCID 89783888, compoundYield 59%

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; 93 mg, 0.329 mmol) and 2,2-dimethylazetidine (84 mg, 0.988 mmol; FCH Group, Chernigov, Ukraine), heating at 100° C. for 4 h. Purification by silica gel (100% DCM to 4% MeOH/DCM) provided 2-(3-(2,2-dimethylazetidin-1-yl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (59% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.66 (s, 6H) 2.27 (t, J=7.53 Hz, 2H) 2.87 (t, J=6.85 Hz, 2H) 3.42 (td, J=6.75, 2.15 Hz, 2H) 4.14 (br. s., 2H) 6.95 (br. s., 1H) 7.12 (d, J=2.15 Hz, 1H) 7.36 (t, J=7.73 Hz, 1H) 7.64 (d, J=8.02 Hz, 1H) 7.95 (d, J=7.43 Hz, 1H) 8.35 (br. s., 1H) 12.09 (br. s., 1H). MS (ESI, pos. ion) m/z: 364.1 (M+1).

Workup

  1. customPrepared similarly to that
  2. customPurification by silica gel (100% DCM to 4% MeOH/DCM)

Sources & evidence

ORD record
ord-43ba52ee7ff446fcbdccf46be3064fad
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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