2-Amino-2-methyl-1-propanol → HCID 136500843, compound

HRID 1056088Notes

Reaction equation

HRID 1056088 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:21][C:15]3[N:16]=[CH:17][NH:18][C:19](=[O:20])[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]>CS(C)=O>[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:21][C:15]3[N:16]=[CH:17][NH:18][C:19](=[O:20])[C:14]=3[CH:13]=1)[CH:8]=[CH:7][CH:6]=2)([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 136500842HCID 136500842, compound

Product 1

HCID 136500843HCID 136500843, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Prepared similarly to that described in Example 260 using 6-(3-fluoro-2-methylquinoxalin-5-yl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (Example 264; 60 mg, 0.203 mmol) and 2-amino-2-methylpropanol (81 μl, 0.847 mmol, Sigma-Aldrich) in DMSO (2 mL) at 50° C. for 20 min. The mixture was purified by rpHPLC (Phenomenex Gemini C18 column (100×50 mm, 10 μm), 90 mL/min, 5-30% ACN in water with 0.1% TFA) to give 6-(3-((1-hydroxy-2-methylpropan-2-yl)amino)-2-methylquinoxalin-5-yl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (8.0 mg, 0.022 mmol, 13% yield) as a yellow solid. MS (ESI, pos. ion) m/z: 365.1 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 12.44 (1H, s), 11.86 (1H, br. s.), 8.00 (1H, dd, J=7.5, 1.3 Hz), 7.90 (1H, d, J=3.7 Hz), 7.70 (1H, d, J=8.0 Hz), 7.41 (1H, t, J=7.8 Hz), 7.28 (1H, d, J=2.2 Hz), 5.94 (1H, s), 5.12 (1H, t, J=5.9 Hz), 3.65 (2H, d, J=5.7 Hz), 2.57 (3H, s), 1.54 (6H, s)

Workup

  1. customPrepared similarly to that
  2. customThe mixture was purified by rpHPLC (Phenomenex Gemini C18 column (100×50 mm, 10 μm), 90 mL/min, 5-30% ACN in water with 0.1% TFA)

Sources & evidence

ORD record
ord-3c8acf285042455abff777fe2a115408
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

Loading…