Cyclopropylamine → HCID 71731145, compound

HRID 1056014Notes

Reaction equation

HRID 1056014 reaction equation
F[C:2]1[C:3]([CH3:22])=[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.[CH:23]1([NH2:26])[CH2:25][CH2:24]1>>[CH:23]1([NH:26][C:2]2[C:3]([CH3:22])=[N:4][C:5]3[C:10]([N:11]=2)=[C:9]([C:12]2[NH:20][C:19]4[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=4[CH:13]=2)[CH:8]=[CH:7][CH:6]=3)[CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 897833202-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 71731145HCID 71731145, compoundYield 78%

Conditions

Temperature
100 °C

Procedure

Prepared similarly to that described in Example 131 using 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 126; 55 mg, 0.186 mmol) and cyclopropanamine (25.7 μl, 0.371 mmol, Aldrich), heating at 100° C. for 30 min. Purification by silica gel (100% DCM to 4% MeOH/DCM) provided 2-(3-(cyclopropylamino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (78% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.70-0.75 (m, 2H) 0.96 (dd, J=6.65, 1.96 Hz, 2H) 2.56 (s, 3H) 2.86-2.96 (m, 3H) 3.44 (td, J=6.80, 2.25 Hz, 2H) 6.98 (br. s., 1H) 7.16 (d, J=2.15 Hz, 1H) 7.37 (t, J=7.82 Hz, 1H) 7.58 (d, J=1.17 Hz, 2H) 7.99 (dd, J=7.63, 1.17 Hz, 1H) 12.83 (br. s., 1H). MS (ESI, pos. ion) m/z: 334.2 (M+1).

Workup

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

Sources & evidence

ORD record
ord-c7ab457e25cd42348028e39b33ea90ff
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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