Acetic Anhydride → rac-N-(cis-2-((3-methyl-8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)-2-quinoxalinyl)amino)cyclobutyl)acetamide

HRID 1055886Notes

Reaction equation

[NH2:1][C@H:2]1[CH2:5][CH2:4][C@H:3]1[NH:6][C:7]1[C:8]([CH3:27])=[N:9][C:10]2[C:15]([N:16]=1)=[C:14]([C:17]1[NH:25][C:24]3[CH2:23][CH2:22][NH:21][C:20](=[O:26])[C:19]=3[CH:18]=1)[CH:13]=[CH:12][CH:11]=2.CCN(C(C)C)C(C)C.[CH3:37][C:38](OC(C)=O)=[O:39]>C(Cl)Cl>[CH3:27][C:8]1[C:7]([NH:6][C@H:3]2[CH2:4][CH2:5][C@H:2]2[NH:1][C:38](=[O:39])[CH3:37])=[N:16][C:15]2[C:10]([N:9]=1)=[CH:11][CH:12]=[CH:13][C:14]=2[C:17]1[NH:25][C:24]2[CH2:23][CH2:22][NH:21][C:20](=[O:26])[C:19]=2[CH:18]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Prepared according to Example 50, using rac-2-(3-((cis-2-aminocyclobutyl)amino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Ex. 54, 120 mg, 0.331 mmol) and DIPEA (0.173 ml, 0.993 mmol, and Ac2O (0.034 ml, 0.364 mmol) in DCM (13.2 mL, and stirring at 25° C. for 2.5 h. Purification by column chromatography (silica gel) provided rac-N-(cis-2-((3-methyl-8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)-2-quinoxalinyl)amino)cyclobutyl)acetamide (68.3 mg, 29%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.91-11.99 (1H, m) 8.20-8.24 (1H, m) 7.88 (1H, d, J=1.00 Hz) 7.55-7.60 (1H, m) 7.49-7.53 (1H, m) 7.34 (1H, t, J=1.00 Hz) 7.30 (1H, s) 7.03 (1H, s) 4.48-4.59 (2H, m) 3.44-3.51 (2H, m) 2.84-3.02 (3H, m) 2.54 (3H, s) 2.25-2.35 (1H, m) 2.09-2.19 (1H, m) 1.91 (1H, s) 1.70 (1H, s) 1.58-1.67 (1H, m). m/z (ESI, +ve) 405.2 (M+H)+.

Workup

customPrepared
customPurification by column chromatography (silica gel)

Sources & evidence

ORD record: ord-71b308217fb8407ebaa762de88e5eeba
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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