4-amino-N-propylbenzamide → 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

HRID 624262Notes

Reaction equation

HRID 624262 reaction equation
N[C:2]1[CH:13]=[CH:12][C:5]([C:6]([NH:8][CH2:9][CH2:10][CH3:11])=[O:7])=CC=1.[CH2:14]1[C:22]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[CH2:16][NH:15]1.[ClH:23].C1[C:32]2[C:27](=[CH:28][C:29]([C:33]([O:35][CH3:36])=O)=[CH:30][CH:31]=2)CN1>>[Cl:23][C:27]1[CH:32]=[CH:31][C:30]2[N:8]([CH2:9][CH2:10][CH2:11][CH2:9][NH:8][C:6]([N:15]3[CH2:14][C:22]4[CH:21]=[CH:20][N:19]=[CH:18][C:17]=4[CH2:16]3)=[O:7])[C:6](=[O:7])[CH:5]3[CH2:12][CH:13]4[CH2:2][CH2:36][O:35][C:33]34[C:29]=2[CH:28]=1

Participants

4

Reactant 3

HCID 4283444-amino-N-propylbenzamideHCID 15194172,3-dihydro-1H-pyrrolo[3,4-c]pyridineHCID 19828495methyl 2,3-dihydro-1H-isoindole-5-carboxylate hydrochloride

Product 1

HCID 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

Procedure

The title compound was prepared as described in Example 272B, substituting 6-(4-aminobutyl)-9-chloro-3,3a,4,4a-tetrahydro-2H-furo[2′,3′:2,3]cyclobuta[1,2-c]quinolin-5(6H)-one for 4-amino-N-propylbenzamide and 1,3-dihydro-2H-pyrrolo[3,4-c]pyridine for methyl isoindoline-5-carboxylate hydrochloride. 1H NMR (400 MHz, CDCl3) δ ppm 8.58 (s, 1H), 8.54 (d, J=4.9 Hz, 1H), 7.29 (d, J=4.9 Hz, 1H), 7.25 (m, 1H), 7.23 (d, J=2.6 Hz, 1H), 6.92 (d, J=8.9 Hz, 1H), 4.84 (t, J=5.6 Hz, 1H), 4.74 (bs, 4H), 4.46 (t, J=8.1 Hz, 1H), 4.22 (m, 1H), 4.05 (m, 1H), 3.91 (m, 1H), 3.39 (m, 3H), 2.93 (m, 1H), 2.31 (m, 1H), 2.22 (m, 1H), 1.84 (m, 1H), 1.69 (m, 5H); MS (ESI(+)) m/e 467 (M+H)+.

Sources & evidence

ORD record
ord-dc9f826824974f54b5dedcd4bed09ed5
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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