Hydrochloric Acid → N-{4-[7-chloro-1-(2-hydroxyethyl)-3-oxo-1,3-dihydrocyclobuta[c]quinolin-4(2H)-yl]butyl}-1,3-dihydro-2H-pyrrolo[3,4-c]pyridine-2-carboxamide

HRID 624263Notes

Reaction equation

HRID 624263 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([N:19]3[CH2:27][C:26]4[CH:25]=[CH:24][N:23]=[CH:22][C:21]=4[CH2:20]3)=[O:18])[C:7](=[O:28])[CH:6]3[CH2:29][CH:30]4[CH2:31][CH2:32][O:33][C:5]34[C:4]=2[CH:3]=1.[OH-].[Na+].Cl>CN(C)C=O.O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([N:19]3[CH2:27][C:26]4[CH:25]=[CH:24][N:23]=[CH:22][C:21]=4[CH2:20]3)=[O:18])[C:7](=[O:28])[C:6]3[CH2:29][CH:30]([CH2:31][CH2:32][OH:33])[C:5]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68751788N-[4-(9-chloro-5-oxo-2,3,3a,4,4a,5-hexahydro-6H-furo[2',3':2,3]cyclobuta[1,2-c]quinolin-6-yl)butyl]-1,3-dihydro-2H-pyrrolo[3,4-c]pyridine-2-carboxamide

Product 1

HCID 57510867N-{4-[7-chloro-1-(2-hydroxyethyl)-3-oxo-1,3-dihydrocyclobuta[c]quinolin-4(2H)-yl]butyl}-1,3-dihydro-2H-pyrrolo[3,4-c]pyridine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[4-(9-chloro-5-oxo-2,3,3a,4,4a,5-hexahydro-6H-furo[2′,3′:2,3]cyclobuta[1,2-c]quinolin-6-yl)butyl]-1,3-dihydro-2H-pyrrolo[3,4-c]pyridine-2-carboxamide (30 mg, 0.064 mmol) in dimethylformamide (292 uL) and water (292 uL) was added sodium hydroxide (1.679 μl, 0.064 mmol). The solution was stirred for 18 hours and then brought to pH ˜7 by dropwise addition of 1M HCl. Column chromatography of the wet, crude mixture provided the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 8.58 (s, 1H), 8.54 (d, J=5.1 Hz, 1H), 7.54 (d, J=2.4 Hz, 1H), 7.46 (dd, J=9.1, 2.4 Hz, 1H), 7.37 (d, J=9.1 Hz, 1H), 7.25 (m, 1H), 5.06 (t, J=5.7 Hz, 1H) 4.77 (bs, 2H), 4.75 (bs, 2H), 4.33 (t, J=7.4 Hz, 2H), 3.87 (m, 2H), 3.74 (m, 2H), 3.46 (m, 2H), 3.37 (dd, J=14.0, 4.5 Hz, 1H), 2.86 (dd, J=14.0, 1.3 Hz, 1H), 2.27 (m, 1H), 1.97 (m, 1H), 1.82 (m, 2H), 1.71 (m, 2H); MS (ESI(+)) m/e 467 (M+H)+.

Sources & evidence

ORD record
ord-d2dfc7820db24b36b65edbed61a8763a
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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