Diisopropylethylamine → HCID 78161662, compound

HRID 1056185Notes

Reaction equation

HRID 1056185 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.[N:25]1[CH:30]=[CH:29][C:28]([CH:31]([NH2:33])[CH3:32])=[N:27][CH:26]=1.CCN(C(C)C)C(C)C>CS(C)=O>[CH3:22][C:3]1[C:2]([NH:33][CH:31]([C:28]2[CH:29]=[CH:30][N:25]=[CH:26][N:27]=2)[CH3:32])=[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 687544711257106-74-3HCID 897833202-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 78161662HCID 78161662, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

This compound (41 mg, 56% 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) (55 mg, 0.19 mmol), (1-(pyrimidin-4-yl)ethanamine dihydrochloride (73 mg, 0.37 mmol) (ChemBridge Corporation) and DIEA (0.26 mL, 1.48 mmol) in 2 mL of DMSO (heated in a microwave at 160° C. for 30 min)1H NMR (400 MHz, DMSO-d6) δ ppm 11.73 (1H, br.), 9.15 (1H, s), 8.69 (1H, d, J=5.1 Hz), 7.87 (1H, d, J=7.2 Hz), 7.67 (2H, d, J=4.3 Hz), 7.57 (1H, d, J=8.0 Hz), 7.32 (1H, t, J=7.7 Hz), 6.99 (1H, br.), 6.87 (1H, s), 5.27 (1H, m), 3.48 (2H, m), 3.06 (2H, m), 2.69 (3H, s), 1.69 (3H, d, J=6.8 Hz). m/z (ESI, +ve) 400.1 (M+H)+.

Sources & evidence

ORD record
ord-2008c986fcff4171bf0357cedce463ff
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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