Diisopropylethylamine → HCID 78161661, compound

HRID 1056184Notes

Reaction equation

HRID 1056184 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.[N:23]1[CH:28]=[CH:27][N:26]=[CH:25][C:24]=1[CH:29]([NH2:31])[CH3:30].CCN(C(C)C)C(C)C>CS(C)=O>[CH3:22][C:3]1[C:2]([NH:31][CH:29]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][N:23]=2)[CH3:30])=[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

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 185190061-(Pyrazin-2-yl)ethanamineHCID 897833202-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 78161661HCID 78161661, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
165 °C

Procedure

This compound (40 mg, 55% yield) as a yellow crystalline solid was prepared according the procedures described for Example 318, using 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (126) (54 mg, 0.18 mmol), 1-(pyrazin-2-yl)ethanamine (45 mg, 0.36 mmol) (Essen Scientific LLC, cat # ES10-0543) and DIEA (64 μL, 0.36 mmol) in 2 mL of DMSO (heated in a microwave at 165° C. for 45 min). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.81 (1H, br.), 8.87 (1H, m), 8.59 (1H, m), 8.50 (1H, d, J=2.5 Hz), 7.87 (1H, d, J=7.2 Hz), 7.67 (1H, d, J=7.0 Hz), 7.57 (1H, d, J=7.4 Hz), 7.32 (1H, t, J=7.8 Hz), 6.99 (1H, br.), 6.90 (1H, d, J=2.2 Hz), 5.41 (1H, m), 3.48 (2H, m), 3.03 (2H, m), 2.68 (3H, s), 1.74 (3H, d, J=7.0 Hz). m/z (ESI, +ve) 400.1 (M+H)+.

Sources & evidence

ORD record
ord-1cb51fc7c13346539d5edb9ab2fe078f
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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