Hydrochloric Acid → HCID 66603426, compound

HRID 1918481Notes

Reaction equation

HRID 1918481 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5](N2C=CC=CC2=O)=[CH:4][CH:3]=1.C(O[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]1=[O:29])C1C=CC=CC=1.Br[C:31]1[CH:39]=[C:38]2[C:34]([C:35]3[CH2:47][CH2:46][N:45]4[CH:41]([CH2:42][CH2:43][CH2:44]4)[C:36]=3[N:37]2[CH3:40])=CC=1.[ClH:48].CCO[CH2:52][CH3:53]>CO>[ClH:48].[CH3:40][N:37]1[C:36]2[C:35](=[CH:34][CH:38]=[C:39]([N:23]3[CH:28]=[CH:27][C:26]([C:5]4[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=4)=[CH:25][C:24]3=[O:29])[CH:31]=2)[C:47]2[CH2:46][N:45]3[CH:44]([CH2:52][C:53]1=2)[CH2:43][CH2:42][CH2:41]3

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 8247291-(benzyloxy)pyridin-2(1H)-oneHCID 23402537HCID 23402537, compoundHCID 58092314HCID 58092314, compound

Product 1

HCID 66603426HCID 66603426, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to the procedure of Example 2 (step b), except substituting 4-((6-methylpyridin-3-yl)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 25% (60 mg). The white 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 (57 mg, 81%) as a white powder: mp 305° C. (decompose); 1H NMR (500 MHz, CD3OD) δ 9.14 (d, J=2.0 Hz, 1H), 8.82 (dd, J=8.5, 2.0 Hz, 1H), 8.03 (d, J=8.5 Hz, 1H), 7.90 (d, J=7.0 Hz, 1H), 7.64 (d, J=8.5 Hz, 1H), 7.58 (d, J=1.5 Hz, 1H), 7.15 (dd, J=8.5, 2.0 Hz, 1H), 7.07 (d, J=2.0 Hz, 1H), 6.91 (dd, J=7.5, 2.0 Hz, 1H), 4.92 (d, J=14.0 Hz, 1H), 4.39 (d, J=14.0 Hz, 1H), 3.90-3.88 (m, 2H), 3.77 (s, 3H), 3.59 (dd, J=17.0, 4.0 Hz, 1H), 3.41-3.38 (m, 1H), 3.08 (dd, J=16.5, 11.5 Hz, 1H), 2.86 (s, 3H), 2.64-2.61 (m, 1H), 2.39-2.24 (m, 2H), 2.01-1.97 (m, 1H); ESI MS m/z 411 [M+H]+; HPLC (Method A)>99% (AUC), tR=8.9 min.

Workup

  1. customa white solid was obtained in 25% (60 mg)
  2. customThe resulting solid was isolated by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-090dcf161c9144f49fefdbcb9ec32fd9
Source dataset
uspto-grants-2013_12
Patent number
US08618299B2

Reaction notes

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