Diisopropylethylamine → HCID 89783751, compound

HRID 1056331Notes

Reaction equation

HRID 1056331 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.Cl.[CH3:25][C:26]([NH2:35])([CH3:34])[CH2:27][N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.CCN(C(C)C)C(C)C>CS(C)=O.CCOC(C)=O>[CH3:34][C:26]([NH:35][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])[CH2:27][N:28]1[CH2:29][CH2:30][O:31][CH2:32][CH2:33]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 897833202-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-oneHCID 118511951HCID 118511951, compound

Product 1

HCID 89783751HCID 89783751, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (40 mg, 0.13 mmol), 2-methyl-1-morpholinopropan-2-amine dihydrochloride [prepared according to the procedures reported in US 20060035903 A1 (2006)] (62 mg, 0.27 mmol) and DIPEA (0.14 mL, 0.81 mmol) in DMSO (2 mL) in a sealed glass tube was heated at 160° C. in a microwave for 45 min. It was diluted with 50 mL of EtOAc, washed with 5 mL of sat. NaHCO3 followed by 5 mL of brine. The organic solution was concentrated and the residue was purified on a silica gel column (3% MeOH in DCM followed by 3-10% of 2 M NH3 in MeOH in DCM) to provide the title compound (17 mg, 29% yield) as a yellow off white crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.85 (1H, br.), 7.79 (1H, dd, J=7.4, 1.2 Hz), 7.60 (1H, dd, J=8.0, 1.2 Hz), 7.35 (1H, t, J=7.7 Hz), 7.02 (1H, s), 6.96 (1H, s), 6.32 (1H, s), 3.60 (4H, m), 3.44 (2H, td, J=6.9, 2.2 Hz), 3.30 (4H, m), 2.86 (2H, t, J=6.8 Hz), 2.70 (2H, s), 2.58 (3H, s), 1.55 (6H, s). m/z (ESI, +ve) 435.0 (M+H)+.

Workup

  1. customprepared
  2. washwashed with 5 mL of sat. NaHCO3
  3. concentrationThe organic solution was concentrated
  4. customthe residue was purified on a silica gel column (3% MeOH in DCM followed by 3-10% of 2 M NH3 in MeOH in DCM)

Sources & evidence

ORD record
ord-95abea56deaa474e9d4e92a1dde15bab
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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