Hydrochloric Acid → HCID 66603817, compound

HRID 1918491Notes

Reaction equation

HRID 1918491 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:18]=[CH:19][C:20]2[C:25]3[CH:26]4[N:31]([CH2:32][CH2:33][C:24]=3[N:23]([CH3:34])[C:21]=2[CH:22]=1)[CH2:30][CH2:29][CH2:28][CH2:27]4.BrC1C=C2C([C:40]3[CH2:52][CH2:51][N:50]4[CH:46]([CH2:47]CC4)[C:41]=3N2C)=CC=1.[ClH:53].[CH3:54][OH:55]>CCOCC>[ClH:53].[ClH:53].[CH3:34][N:23]1[C:24]2[CH2:33][CH2:32][N:31]3[CH:26]([C:25]=2[C:20]2[CH:19]=[CH:18][C:17]([N:9]4[CH:14]=[CH:13][C:12]([O:55][CH2:54][C:52]5[CH:51]=[N:50][C:46]([CH3:47])=[CH:41][CH:40]=5)=[CH:11][C:10]4=[O:15])=[CH:22][C:21]1=2)[CH2:27][CH2:28][CH2:29][CH2:30]3

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8247291-(benzyloxy)pyridin-2(1H)-oneHCID 58092306HCID 58092306, compoundHCID 58092314HCID 58092314, compound

Product 1

HCID 66603817HCID 66603817, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

According to the procedure of Example 2 (step b), except substituting 4-((6-methylpyridin-3-yl)methoxy)pyridin-2(1H)-one for 4-(benzyloxypyridin-2(1H)-one and substituting 10-bromo-8-methyl-1,2,3,4,6,7,8,12c-octahydroindolo[3,2-a]quinolizine for 9-bromo-11-methyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole, a pale yellow solid was obtained in 37% (40 mg). The pale yellow solid was dissolved in CH3OH (1 mL) and treated with 2 N HCl in Et2O (1 mL). The solvent was removed under reduced pressure, and the resulting solid was dried under vacuum to give the title compound (45 mg, 97%) as a pale yellow powder: mp 210-214° C.; 1H NMR (500 MHz, CD3OD) δ 8.87 (d, J=1.5 Hz, 1H), 8.62 (dd, J=8.5, 2.0 Hz, 1H), 8.01 (d, J=8.5 Hz, 1H), 7.73 (d, J=8.5 Hz, 1H), 7.64 (d, J=8.0 Hz, 1H), 7.49 (d, J=2.0 Hz, 1H), 7.05 (dd, J=8.5, 2.0 Hz, 1H), 6.35 (dd, J=7.5, 2.5 Hz, 1H), 6.18 (d, J=2.5 Hz, 1H), 5.39 (s, 2H), 4.67 (d, J=11.5 Hz, 1H), 3.81 (dd, J=12.5, 6.0 Hz, 1H), 3.73 (s, 3H), 3.65-3.62 (m, 2H), 3.40-3.37 (m, 2H), 3.22 (dd, J=17.5, 5.5 Hz, 1H), 3.11 (d, J=14.5 Hz, 1H), 2.83 (s, 3H), 2.10-1.79 (m, 5H); ESI MS m/z 455 [M+H]+; HPLC (Method A) 97.2% (AUC), tR=9.4 min.

Workup

  1. customa pale yellow solid was obtained in 37% (40 mg)
  2. customThe solvent was removed under reduced pressure
  3. customthe resulting solid was dried under vacuum

Sources & evidence

ORD record
ord-3f050d9df8c740dfbcf66bc0ffc4b1fd
Source dataset
uspto-grants-2013_12
Patent number
US08618299B2

Reaction notes

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