Hydrochloric Acid → HCID 66603692, compound

HRID 1918489Notes

Reaction equation

HRID 1918489 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:21]3[CH:33]4[N:29]([CH2:30][CH2:31][CH2:32]4)[CH2:28][CH2:27][C:22]=3[N:23]([CH3:26])[C:24]=2[CH:25]=1.BrC1C=C2C([C:39]3[CH2:51][CH2:50][N:49]4[CH:45]([CH2:46]CC4)[C:40]=3N2C)=CC=1.[ClH:52].[CH3:53][OH:54]>CCOCC>[ClH:52].[ClH:52].[CH3:26][N:23]1[C:24]2[CH:25]=[C:17]([N:9]3[CH:14]=[CH:13][C:12]([O:54][CH2:53][C:51]4[CH:50]=[N:49][C:45]([CH3:46])=[CH:40][CH:39]=4)=[CH:11][C:10]3=[O:15])[CH:18]=[CH:19][C:20]=2[C:21]2[CH:33]3[N:29]([CH2:28][CH2:27][C:22]1=2)[CH2:30][CH2:31][CH2:32]3

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8247291-(benzyloxy)pyridin-2(1H)-oneHCID 58092314HCID 58092314, compoundHCID 66603379HCID 66603379, compound

Product 1

HCID 66603692HCID 66603692, compoundYield 81%

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 9-bromo-7-methyl-2,3,5,6,7,11c-hexahydro-1H-indolizino[7,8-b]indole for 9-bromo-11-methyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole, a yellow solid was obtained in 25% (72 mg). The yellow solid was dissolved in CH3OH (1 mL) and 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 (68 mg, 81%) as a yellow-brown powder: mp 280-282° C.; 1H NMR (500 MHz, CD3OD) δ 8.55 (d, J=2.0 Hz, 1H), 7.91 (dd, J=8.0, 2.0 Hz, 1H), 7.61 (d, J=8.5 Hz, 1H), 7.59 (d, J=7.5 Hz, 1H), 7.48 (d, J=2.0 Hz, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.06 (dd, J=8.5, 2.0 Hz, 1H), 6.29 (dd, J=7.5, 2.5 Hz, 1H), 6.15 (d, J=2.5 Hz, 1H), 5.22 (s, 2H), 5.11 (br s, 1H), 3.74 (s, 3H), 3.74-3.72 (m, 4H), 3.47-3.44 (m, 1H), 3.24-3.22 (m, 1H), 2.73-2.71 (m, 1H), 2.59 (s, 3H), 2.25-2.17 (m, 3H); ESI MS m/z 441 [M+H]+; HPLC (Method A)>99% (AUC), tR=9.2 min.

Workup

  1. customa yellow solid was obtained in 25% (72 mg)
  2. customThe resulting solid was isolated by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-f2a29e1b792c4de798f8175f41179f03
Source dataset
uspto-grants-2013_12
Patent number
US08618299B2

Reaction notes

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