Hydrochloric Acid → HCID 66603040, compound

HRID 1918499Notes

Reaction equation

HRID 1918499 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[CH2:25][CH:26]4[N:31]([CH2:32][C:33]=3[C:20]2=[CH:19][CH:18]=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[CH2:25][CH:26]3[N:31]([CH2:32][C:33]=2[C:20]2[C:21]1=[CH:22][C:17]([N:9]1[CH:14]=[CH:13][C:12]([O:55][CH2:54][C:52]4[CH:51]=[N:50][C:46]([CH3:47])=[CH:41][CH:40]=4)=[CH:11][C:10]1=[O:15])=[CH:18][CH:19]=2)[CH2:30][CH2:29][CH2:28][CH2:27]3

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8247291-(benzyloxy)pyridin-2(1H)-oneHCID 58092305HCID 58092305, compoundHCID 58092314HCID 58092314, compound

Product 1

HCID 66603040HCID 66603040, compoundYield 71%

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 3-bromo-5-methyl-5,6,6a,7,8,9,10,12-octahydroindolo[2,3-b]quinolizine for 9-bromo-11-methyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole, a yellow solid was obtained in 43% (92 mg). The 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 (75 mg, 71%) as a white powder: mp 270-272° C.; 1H NMR (500 MHz, CD3OD) δ 8.63 (s, 1H), 8.08 (d, J=7.5 Hz, 1H), 7.60 (d, J=7.5 Hz, 1H), 7.58 (d, J=8.5 Hz, 1H), 7.56 (d, J=10.0 Hz, 1H), 7.47 (d, J=1.5 Hz, 1H), 7.06 (dd, J=8.5, 2.0 Hz, 1H), 6.31 (dd, J=7.5, 2.5 Hz, 1H), 6.16 (d, J=2.5 Hz, 1H), 5.26 (s, 2H), 4.75 (d, J=14.5 Hz, 1H), 4.37 (d, J=14.0 Hz, 1H), 3.81-3.78 (m, 1H), 3.74 (s, 3H), 3.72-3.66 (m, 1H), 3.40 (dd, J=17.5, 4.5 Hz, 1H), 3.26-3.23 (m, 1H), 2.99 (dd, J=18.0, 11.0 Hz, 1H), 2.64 (s, 3H), 2.36-2.33 (m, 1H), 2.09-1.98 (m, 2H), 1.85-1.71 (m, 3H); ESI MS m/z 455 [M+H]+; HPLC (Method A)>99.0% (AUC), tR=9.3 min.

Workup

  1. customa yellow solid was obtained in 43% (92 mg)
  2. customThe solvent was removed under reduced pressure
  3. customthe resulting solid was dried under vacuum

Sources & evidence

ORD record
ord-11e92499f15147fab8137de7a4a8180f
Source dataset
uspto-grants-2013_12
Patent number
US08618299B2

Reaction notes

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