Trifluoroacetic acid → (R)-2-(2-methyl-3-(pyrrolidin-3-ylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

HRID 1055889Notes

Reaction equation

C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]2[C:23]([CH3:24])=[N:22][C:21]3[C:16](=[C:17]([C:25]4[NH:33][C:32]5[CH2:31][CH2:30][NH:29][C:28](=[O:34])[C:27]=5[CH:26]=4)[CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:24][C:23]1[C:14]([NH:13][C@@H:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)=[N:15][C:16]2[C:21](=[CH:20][CH:19]=[CH:18][C:17]=2[C:25]2[NH:33][C:32]3[CH2:31][CH2:30][NH:29][C:28](=[O:34])[C:27]=3[CH:26]=2)[N:22]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Prepared according to Example 53, using (R)-tert-butyl-3-((3-methyl-8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinoxalin-2-yl)amino)pyrrolidine-1-carboxylate (Ex. 48, 150 mg, 0.506 mmol), and TFA (940 μl, 12.66 mmol) in DCM (20 mL), stirring at 25° C. for 1.5 h. Purification by column chromatography (silica gel: 0 to 10% MeOH/DCM) provided (R)-2-(2-methyl-3-(pyrrolidin-3-ylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (140 mg, 76%). 1H NMR (DMSO-d6) δ: 12.20 (s, 1H), 7.85-7.92 (m, 1H), 7.54-7.61 (m, 1H), 7.28-7.37 (m, 1H), 7.12 (s, 1H), 6.95 (s, 2H), 4.40-4.52 (m, 1H), 3.40-3.51 (m, 3H), 3.09-3.14 (m, 1H), 2.94-3.07 (m, 2H), 2.88 (s, 3H), 2.58-2.69 (m, 1H), 2.11-2.23 (m, 1H), 1.81-1.95 (m, 1H). m/z (ESI, +ve) 363.2 (M+H)+.

Workup

customPrepared
customPurification by column chromatography (silica gel: 0 to 10% MeOH/DCM)

Sources & evidence

ORD record: ord-2832c6720af74d13be7f37645614f38f
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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