Hydrochloric Acid → HCID 68656833, compound

HRID 930770Notes

Reaction equation

HRID 930770 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)=[CH:11][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)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 50908738HCID 50908738, compound

Product 1

HCID 68656833HCID 68656833, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2 N HCl in Et2O (0.12 mL, 0.24 mmol) was added to a solution of 4-(4-methoxyphenyl)-1-(5-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)pyridin-2(1H)-one (45 mg, 0.12 mmol) in CH2Cl2 (2.0 mL), and the solution was stirred at ambient temperature for 2.5 h under N2. The reaction mixture was concentrated, partially diluted with H2O and lyophilized to provide the title compound (46 mg, 95%) as a yellow powder: 1H NMR (500 MHz, DMSO-d6) δ 9.26 (br s, 2H), 7.76 (d, J=9.0 Hz, 2H), 7.70 (d, J=7.0 Hz, 1H), 7.60-7.57 (m, 2H), 7.09-7.06 (m, 3H), 6.73 (d, J=2.0 Hz, 1H), 6.68 (dd, J=7.5, 2.0 Hz, 1H), 4.37-4.35 (m, 2H), 3.83 (s, 3H), 3.70 (s, 3H), 3.54-3.53 (m, 2H), 3.10 (t, J=6.0 Hz, 2H); ESI MS m/z 386 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionpartially diluted with H2O

Sources & evidence

ORD record
ord-a96aff8bc37d4734865a88e1b6e9dfec
Source dataset
uspto-grants-2016_03
Patent number
US09296743B2

Reaction notes

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