Acetic Anhydride → HCID 89783436, compound

HRID 1055968Notes

Reaction equation

HRID 1055968 reaction equation
[CH3:1][C:2](OC(C)=O)=[O:3].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[NH:15]1[CH2:18][CH:17]([NH:19][C:20]2[C:21]([CH3:40])=[N:22][C:23]3[C:28]([N:29]=2)=[C:27]([C:30]2[NH:38][C:37]4[CH2:36][CH2:35][NH:34][C:33](=[O:39])[C:32]=4[CH:31]=2)[CH:26]=[CH:25][CH:24]=3)[CH2:16]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[C:2]([N:15]1[CH2:16][CH:17]([NH:19][C:20]2[C:21]([CH3:40])=[N:22][C:23]3[C:28]([N:29]=2)=[C:27]([C:30]2[NH:38][C:37]4[CH2:36][CH2:35][NH:34][C:33](=[O:39])[C:32]=4[CH:31]=2)[CH:26]=[CH:25][CH:24]=3)[CH2:18]1)(=[O:3])[CH3:1]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 89784319HCID 89784319, compound

Product 1

HCID 89783436HCID 89783436, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Ac2O (4.49 μl, 0.048 mmol) was added to a mixture of 2-(3-(azetidin-3-ylamino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one 2,2,2-trifluoroacetate (20.0 mg, 0.043 mmol) and DIPEA (0.023 mL, 0.130 mmol) in DCM (1.0 mL), and the resulting yellow suspension was stirred at 25° C. for 10 min. The mixture was concentrated in vacuo, and the residue was taken up in in DMSO (2.0 mL) and purified by reversed-phase HPLC (Phenomenex Gemini C18 column (150×30 mm, 10 μm), 35 mL/min, 5-100% ACN/H2O+0.1% TFA) to provide 2-(3-((1-acetylazetidin-3-yl)amino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one 2,2,2-trifluoroacetate (19.0 mg, 0.038 mmol, 87% yield) as a red solid: 1H NMR (400 MHz, MeOH-d4) δ ppm 7.86 (1H, d, J=7.4 Hz), 7.66 (1H, d, J=7.4 Hz), 7.44 (1H, t, J=7.8 Hz), 7.18 (1H, s), 4.89-4.97 (1H, m), 4.69 (1H, t, J=8.3 Hz), 4.46 (1H, dd, J=9.9, 8.1 Hz), 4.23 (1H, dd, J=9.2, 5.1 Hz), 4.05 (1H, dd, J=10.4, 5.1 Hz), 3.64 (2H, t, J=7.1 Hz), 3.04 (2H, t, J=7.0 Hz), 2.66 (3H, s), 1.91 (3H, s). 19F NMR (376 MHz, MeOH-d4) δ ppm −77.73 (3F, s). m/z (ESI, +ve) 391.1 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by reversed-phase HPLC (Phenomenex Gemini C18 column (150×30 mm, 10 μm), 35 mL/min, 5-100% ACN/H2O+0.1% TFA)

Sources & evidence

ORD record
ord-d983876274274a19afac86ed2194d8e2
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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