Hydrochloric Acid → HCID 68657573, compound

HRID 930766Notes

Reaction equation

HRID 930766 reaction equation
Cl.CCOCC.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][N:17]([C:20]3[CH:28]=[C:27]4[C:23]([C:24]5[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][C:25]=5[N:26]4[CH3:29])=[CH:22][CH:21]=3)[C:16](=[O:35])[CH:15]=2)=[C:10]([O:36][CH3:37])[CH:9]=1>C(Cl)Cl>[ClH:7].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][N:17]([C:20]3[CH:28]=[C:27]4[C:23]([C:24]5[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][C:25]=5[N:26]4[CH3:29])=[CH:22][CH:21]=3)[C:16](=[O:35])[CH:15]=2)=[C:10]([O:36][CH3:37])[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 57950316HCID 57950316, compound

Product 1

HCID 68657573HCID 68657573, compoundYield 135.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2 N HCl in Et2O (0.17 mL, 0.34 mmol) was added to a solution of 4-(4-chloro-2-methoxyphenyl)-1-(2,9-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-7-yl)pyridin-2(1H)-one (74 mg, 0.17 mmol) in CH2Cl2 (2 mL) and the reaction was stirred at ambient temperature for 1.5 h under N2. The solids were collected by filtration, washed with Et2O and dried under reduced pressure to yield the title compound (54 mg, 68%) as a yellow powder: mp 272-280° C.; 1H NMR (500 MHz, DMSO-d6) δ 10.82 (br s, 1H), 7.65 (d, J=7.0 Hz, 1H), 7.62 (d, J=1.5 Hz, 1H), 7.60 (d, J=8.5 Hz, 1H), 7.44 (d, J=8.5 Hz, 1H), 7.26 (d, J=1.5 Hz, 1H), 7.14-7.09 (m, 2H), 6.56 (d, J=1.5 Hz, 1H), 6.47 (dd, J=7.0, 1.5 Hz, 1H), 4.79-4.76 (m, 1H), 4.53-4.42 (m, 1H), 3.87 (s, 3H), 3.72-3.68 (m, 4H), 3.42-3.40 (m, 1H), 3.08-3.06 (m, 2H), 3.00 (s, 3H); ESI MS m/z 434 [M+H]+; HPLC (Method A) 96.5% (AUC), tR=15.3 min.

Workup

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

Sources & evidence

ORD record
ord-aeb6830200df4454b184806158281191
Source dataset
uspto-grants-2016_03
Patent number
US09296743B2

Reaction notes

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