Hydrochloric Acid → HCID 66603365, compound

HRID 1918497Notes

Reaction equation

HRID 1918497 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:25]=[C:24]2[C:20]([C:21]3[CH2:33][N:32]4[CH:28]([CH2:29][CH2:30][CH2:31]4)[CH2:27][C:22]=3[N:23]2[CH3:26])=[CH:19][CH:18]=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].[CH3:26][N:23]1[C:24]2[C:20](=[CH:19][CH:18]=[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:25]=2)[C:21]2[CH2:33][N:32]3[CH:28]([CH2:27][C:22]1=2)[CH2:29][CH2:30][CH2:31]3

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8247291-(benzyloxy)pyridin-2(1H)-oneHCID 58092314HCID 58092314, compoundHCID 66603353HCID 66603353, compound

Product 1

HCID 66603365HCID 66603365, compoundYield 64%

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 8-bromo-10-methyl-2,3,5,10,11,11a-hexahydro-1H-indolizino[7,6-b]indole for 9-bromo-11-methyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole, a white solid was obtained in 31% (81 mg). The yellow solid 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 (60 mg, 64%) as a white powder: mp 260-263° C.; 1H NMR (500 MHz, CD3OD) δ 8.70 (d, J=1.5 Hz, 1H), 8.25 (d, J=7.5 Hz, 1H), 7.70 (d, J=8.0 Hz, 1H), 7.62 (d, J=7.5 Hz, 1H), 7.59 (d, J=8.5 Hz, 1H), 7.48 (d, J=1.5 Hz, 1H), 7.06 (dd, J=8.5, 2.0 Hz, 1H), 6.32 (dd, J=7.5, 3.0 Hz, 1H), 6.16 (d, J=2.5 Hz, 1H), 5.30 (s, 2H), 4.90 (d, J=14.0 Hz, 1H), 4.37 (d, J=14.0 Hz, 1H), 3.84-3.91 (m, 2H), 3.75 (s, 3H), 3.57 (dd, J=17.0, 4.0 Hz, 1H), 3.41-3.39 (m, 1H), 3.06 (dd, J=16.5, 11.5 Hz, 1H), 2.70 (s, 3H), 2.63-2.60 (m, 1H), 2.38-2.23 (m, 2H), 1.99-1.95 (m, 1H); ESI MS m/z 441 [M+H]+; HPLC (Method A) 97.7% (AUC), tR=9.1 min.

Workup

  1. customa white solid was obtained in 31% (81 mg)
  2. customThe resulting solid was isolated by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-717e25d465da44daa6174fa45b2607c8
Source dataset
uspto-grants-2013_12
Patent number
US08618299B2

Reaction notes

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