Isopropylamine → HCID 89784273, compound

HRID 1056012Notes

Reaction equation

HRID 1056012 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.[CH3:23][CH:24]([NH2:26])[CH3:25]>>[CH:24]([NH:26][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)([CH3:25])[CH3:23]

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 897833202-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 89784273HCID 89784273, compoundYield 47%

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; 45 mg, 0.152 mmol) and propan-2-amine (38.8 μl, 0.456 mmol, Aldrich), heating at 100° C. for 30 min. Purification by silica gel (100% DCM to 3% MeOH/DCM) provided 2-(3-(isopropylamino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4 (5H)-one (47% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.38 (d, J=6.46 Hz, 6H) 2.56 (s, 3H) 2.90 (t, J=6.85 Hz, 2H) 3.45 (td, J=6.80, 2.25 Hz, 2H) 4.30 (dq, J=13.23, 6.48 Hz, 1H) 6.88 (d, J=7.04 Hz, 1H) 6.96 (br. s., 1H) 7.12 (s, 1H) 7.33 (t, J=7.82 Hz, 1H) 7.57 (dd, J=7.92, 1.27 Hz, 1H) 7.90 (dd, J=7.63, 1.17 Hz, 1H) 12.23 (br. s., 1H). MS (ESI, pos. ion) m/z: 336.0 (M+1).

Workup

  1. customPrepared similarly to that
  2. customPurification by silica gel (100% DCM to 3% MeOH/DCM)

Sources & evidence

ORD record
ord-c40a896ae6134deaaf7ce8a580b75d20
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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