Hydrochloric Acid → HCID 68657714, compound

HRID 930773Notes

Reaction equation

HRID 930773 reaction equation
[ClH:1].CCOCC.[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][N:18]([C:21]3[CH:22]=[CH:23][C:24]4[C:25]5[CH2:34][NH:33][CH2:32][CH2:31][C:26]=5[N:27]([CH3:30])[C:28]=4[CH:29]=3)[C:17](=[O:35])[CH:16]=2)=[C:11]([CH3:36])[CH:10]=1>C(Cl)Cl>[ClH:1].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][N:18]([C:21]3[CH:22]=[CH:23][C:24]4[C:25]5[CH2:34][NH:33][CH2:32][CH2:31][C:26]=5[N:27]([CH3:30])[C:28]=4[CH:29]=3)[C:17](=[O:35])[CH:16]=2)=[C:11]([CH3:36])[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 52947558HCID 52947558, compound

Product 1

HCID 68657714HCID 68657714, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2 N HCl in Et2O (0.40 mL, 0.80 mmol) was added to a solution of 4-(4-methoxy-2-methylphenyl)-1-(5-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)pyridin-2(1H)-one (0.16 g, 0.40 mmol) in CH2Cl2 (1.5 mL), and the solution was stirred at ambient temperature for 1 h under N2. The solids were collected by filtration, washed with Et2O and dried to yield the title compound (0.15 g, 85%) as an off-white powder: 1H NMR (500 MHz, DMSO-d6) δ 9.39 (br s, 2H), 7.67 (d, J=7.0 Hz, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.27 (d, J=2.0 Hz, 1H), 7.25 (d, J=8.5 Hz, 1H), 7.10 (dd, J=8.5, 2.0 Hz, 1H), 6.92 (d, J=2.5 Hz, 1H), 6.88 (dd, J=8.0, 2.5 Hz, 1H), 6.37 (d, J=2.0 Hz, 1H), 6.34 (dd, J=7.0, 2.0 Hz, 1H), 4.36-4.34 (m, 2H), 3.79 (s, 3H), 3.71 (s, 3H), 3.53-3.52 (m, 2H), 3.10 (t, J=6.0 Hz, 2H), 2.35 (s, 3H); ESI MS m/z 400 [M+H]+; HPLC (Method A) 95.8% (AUC), tR=14.5 min.

Workup

  1. filtrationThe solids were collected by filtration
  2. washwashed with Et2O
  3. customdried

Sources & evidence

ORD record
ord-ca24be5998ab433bb165d4ddc3980841
Source dataset
uspto-grants-2016_03
Patent number
US09296743B2

Reaction notes

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