Diisopropylethylamine → HCID 178432137, compound

HRID 1056026Notes

Reaction equation

HRID 1056026 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.[NH2:23][C@@H:24]1[CH2:29][CH2:28][C@H:27]([OH:30])[CH2:26][CH2:25]1.CCN(C(C)C)C(C)C>>[OH:30][C@@H:27]1[CH2:28][CH2:29][C@H:24]([NH:23][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][CH2:26]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 897833202-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-oneHCID 178511714HCID 178511714, compound

Product 1

HCID 178432137HCID 178432137, compoundYield 26%

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; 41 mg, 0.138 mmol), cis-4-aminocyclohexanol (42.0 mg, 0.277 mmol, J&W Pharmlab, Levittown, Pa.), and DIPEA (121 μl, 0.692 mmol), heating at 100° C. for 1 h. Purification by silica gel (100% DCM to 10% MeOH/DCM) provided 2-(3-((cis-4-hydroxycyclohexyl)amino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (26% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.61-1.71 (m, 2H) 1.72-1.83 (m, 4H) 1.83-1.96 (m, 2H) 2.56 (s, 3H) 2.89 (t, J=6.85 Hz, 2H) 3.41-3.48 (m, 2H) 3.88 (br. s., 1H) 3.97-4.07 (m, 1H) 4.42 (br. s., 1H) 6.77 (d, J=7.04 Hz, 1H) 6.91 (br. s., 1H) 7.18 (d, J=1.76 Hz, 1H) 7.31 (t, J=7.82 Hz, 1H) 7.55 (d, J=7.82 Hz, 1H) 7.87 (d, J=7.63 Hz, 1H) 11.94 (br. s., 1H). MS (ESI, pos. ion) m/z: 392.1 (M+1).

Workup

  1. customPrepared similarly to that
  2. customPurification by silica gel (100% DCM to 10% MeOH/DCM)

Sources & evidence

ORD record
ord-bc18cde63584498397e5b623ebd28c03
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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