Hydrochloric Acid → HCID 66603452, compound

HRID 1918475Notes

Reaction equation

HRID 1918475 reaction equation
C(O[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=[O:15])C1C=CC=CC=1.Br[C:17]1[CH:22]=[C:21]2[N:23]([CH3:34])[C:24]3[CH:33]4[N:28]([CH2:29][CH2:30][CH2:31][CH2:32]4)[CH2:27][CH2:26][C:25]=3[C:20]2=[CH:19][CH:18]=1.BrC1C=C2C([C:40]3[CH2:52][CH2:51][N:50]4[CH:46]([CH2:47]CC4)[C:41]=3N2C)=CC=1.[ClH:53].C[OH:55]>CCOCC>[ClH:53].[Cl:53][C:52]1[CH:40]=[CH:41][C:46]([CH2:47][O:55][C:12]2[CH:13]=[CH:14][N:9]([C:17]3[CH:22]=[C:21]4[N:23]([CH3:34])[C:24]5[CH:33]6[N:28]([CH2:29][CH2:30][CH2:31][CH2:32]6)[CH2:27][CH2:26][C:25]=5[C:20]4=[CH:19][CH:18]=3)[C:10](=[O:15])[CH:11]=2)=[N:50][CH:51]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8247291-(benzyloxy)pyridin-2(1H)-oneHCID 58092300Indolo[2,3-a]quinolizine, 10-bromo-1,2,3,4,6,7,12,12b-octahydro-12-methyl-HCID 58092314HCID 58092314, compound

Product 1

HCID 66603452HCID 66603452, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

According to the procedure of Example 2 (step b), except substituting 4-((5-chloropyridin-2-yl)methoxy)pyridin-2(1H)-one for 4-(benzyloxypyridin-2(1H)-one and substituting 10-Bromo-12-methyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine for 9-bromo-11-methyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole, a yellow oil was obtained in 23% (46 mg). The yellow oil was dissolved in CH3OH (1 mL) and was treated with 2 N HCl in Et2O (1 mL). The resulting solid was isolated by filtration and dried under vacuum to give the title compound (47 mg, 95%) as a yellow-brown solid: mp 204-208° C.; 1H NMR (500 MHz, CD3OD) δ 8.63 (s, 1H), 7.97 (dd, J=8.5, 2.5 Hz, 1H), 7.65-7.63 (m, 3H), 7.48 (d, J=1.5 Hz, 1H), 7.06 (dd, J=8.0, 2.0 Hz, 1H), 6.39 (dd, J=7.5, 3.0 Hz, 1H), 6.16 (d, J=3.0 Hz, 1H), 5.30 (s, 2H), 4.91 (dd, J=12.0, 3.5 Hz, 1H), 4.13-4.09 (m, 1H), 3.74 (s, 3H), 3.66-3.60 (m, 3H), 3.22-3.19 (m, 2H), 2.34-2.31 (m, 1H), 2.11-2.01 (m, 3H), 1.91-1.85 (m, 2H); ESI MS m/z 475 [M+H]+; HPLC (Method A) 97.7% (AUC), tR=12.8 min.

Workup

  1. customa yellow oil was obtained in 23% (46 mg)
  2. customThe resulting solid was isolated by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-805cc4057be44560bdb416bee566adc7
Source dataset
uspto-grants-2013_12
Patent number
US08618299B2

Reaction notes

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