Diisopropylethylamine → HCID 89783585, compound

HRID 1056018Notes

Reaction equation

HRID 1056018 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.Cl.[NH2:24][CH:25]1[CH2:30][NH:29][C:28](=[O:31])[CH2:27][CH2:26]1.CCN(C(C)C)C(C)C>>[CH3:22][C:3]1[C:2]([NH:24][CH:25]2[CH2:26][CH2:27][C:28](=[O:31])[NH:29][CH2:30]2)=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:12]2[NH:20][C:19]3[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=3[CH:13]=2)[N:4]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 470029405-Aminopiperidin-2-one--hydrogen chloride (1/1)HCID 897833202-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 89783585HCID 89783585, compoundYield 33%

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; 48 mg, 0.162 mmol), rac-5-aminopiperidin-2-one hydrochloride (48.8 mg, 0.324 mmol, Advanced ChemBlocks, Inc., Burlingame, Calif.), and DIPEA (141 μl, 0.810 mmol), heating at 100° C. for 1.5 h. Purification by silica gel (100% DCM to 20% MeOH/DCM) provided rac-2-(2-methyl-3-((6-oxopiperidin-3-yl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (33% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.93-2.07 (m, 1H) 2.14-2.23 (m, 1H) 2.31-2.41 (m, 1H) 2.58 (s, 3H) 2.83-2.90 (m, 2H) 3.23-3.29 (m, 1H) 3.44 (td, J=6.85, 2.15 Hz, 2H) 3.51-3.59 (m, 1H) 4.39-4.51 (m, 1H) 6.94 (br. s., 1H) 7.00 (d, J=6.65 Hz, 1H) 7.13 (s, 1H) 7.37 (t, J=7.82 Hz, 1H) 7.50 (d, J=2.15 Hz, 1H) 7.61 (d, J=7.04 Hz, 1H) 7.89 (d, J=7.63 Hz, 1H) 11.90 (br. s., 1H). MS (ESI, pos. ion) m/z: 391.3 (M+1).

Workup

  1. customPrepared similarly to that
  2. customPurification by silica gel (100% DCM to 20% MeOH/DCM)

Sources & evidence

ORD record
ord-1ba57390e49143fdaac2061fafa82e58
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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