Diisopropylethylamine → HCID 78161660, compound

HRID 1056183Notes

Reaction equation

HRID 1056183 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][CH:26]=[CH:25][C:24]=1[CH:29]([NH2:31])[CH3:30].CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[CH3:22][C:3]1[C:2]([NH:31][CH:29]([C:24]2[CH:25]=[CH: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 5418771-(Pyridin-2-yl)ethan-1-amineHCID 897833202-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 78161660HCID 78161660, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

This compound (16 mg, 44% 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) (27 mg, 0.09 mmol), 1-(2-pyridyl)ethylamine (16.7 mg, 0.14 mmol) [Matrix Scientific, cat# 012223] and DIEA (24 μL, 0.13 mmol) in 2 mL of NMP (heated in a microwave at 150° C. for 30 min)1H NMR (400 MHz, DMSO-d6) δ ppm 12.08 (1H, br.), 8.51 (1H, d, J=4.5 Hz), 7.89 (1H, d, J=7.4 Hz), 7.77 (1H, m), 7.62 (2H, m), 7.55 (1H, d, J=7.8 Hz), 7.33 (1H, m), 7.21 (1H, m), 7.00 (1H, br.), 6.90 (1H, d, J=2.0 Hz), 5.31 (1H, t, J=7.1 Hz), 3.47 (2H, m), 3.11 (2H, m), 2.70 (3H, s), 1.69 (3H, d, J=7.0 Hz). m/z (EST, +ve) 399.0 (M+H)+.

Sources & evidence

ORD record
ord-b38e571466ec4745be342414aac0df3d
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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