2-Amino-2-methyl-1-propanol → HCID 71731273, compound

HRID 1056020Notes

Reaction equation

HRID 1056020 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:24]([CH3:28])([CH3:27])[CH2:25][OH:26]>>[OH:26][CH2:25][C:24]([NH:23][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)([CH3:28])[CH3:27]

Participants

3

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 897833202-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 71731273HCID 71731273, compoundYield 17%

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) and 2-amino-2-methylpropan-1-ol (31.1 μl, 0.324 mmol, Sigma-Aldrich), heating at 100° C. for 1.5 h. Purification by silica gel (100% DCM to 6% MeOH/DCM) provided 2-(3-((1-hydroxy-2-methylpropan-2-yl)amino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (17% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.52 (s, 6H) 2.56 (s, 3H) 2.88 (t, J=6.94 Hz, 2H) 3.45 (td, J=6.80, 2.45 Hz, 2H) 3.66 (d, J=5.28 Hz, 2H) 5.15 (t, J=5.58 Hz, 1H) 5.87 (s, 1H) 6.96 (br. s., 1H) 7.03 (d, J=2.15 Hz, 1H) 7.35 (t, J=7.82 Hz, 1H) 7.59 (dd, J=8.02, 1.37 Hz, 1H) 7.84 (dd, J=7.43, 1.37 Hz, 1H) 12.03 (br. s., 1H). MS (ESI, pos. ion) m/z: 366.0 (M+1).

Workup

  1. customPrepared similarly to that
  2. customPurification by silica gel (100% DCM to 6% MeOH/DCM)

Sources & evidence

ORD record
ord-36823310b71741ac9a82a9593c566040
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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