Hydrochloric Acid → HCID 68656848, compound

HRID 930762Notes

Reaction equation

HRID 930762 reaction equation
[ClH:1].CCOCC.[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][N:18]([C:21]2[CH:29]=[C:28]3[C:24]([C:25]4[CH2:34][CH2:33][N:32]([CH2:35][CH2:36][N:37]5[CH2:41][CH2:40][CH2:39][CH2:38]5)[CH2:31][C:26]=4[N:27]3[CH3:30])=[CH:23][CH:22]=2)[C:17](=[O:42])[CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(Cl)Cl>[ClH:1].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][N:18]([C:21]2[CH:29]=[C:28]3[C:24]([C:25]4[CH2:34][CH2:33][N:32]([CH2:35][CH2:36][N:37]5[CH2:38][CH2:39][CH2:40][CH2:41]5)[CH2:31][C:26]=4[N:27]3[CH3:30])=[CH:23][CH:22]=2)[C:17](=[O:42])[CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 579502654-(Benzyloxy)-1-(9-methyl-2-(2-(pyrrolidin-1-yl)ethyl)-2,3,4,9,-tetrahydro-1h-pyrido[3,4-b]indol-7-yl)pyridine-2(1h)-one

Product 1

HCID 68656848HCID 68656848, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2 N HCl in Et2O (20 μL, 0.04 mmol) was added to a solution of 4-(benzyloxy)-1-(9-methyl-2-(2-(pyrrolidin-1-yl)ethyl)-2,3,4,9,-tetrahydro-1H-pyrido[3,4-b]indol-7-yl)pyridine-2(1H)-one (10 mg, 0.020 mmol) in CH2Cl2 (3 mL) and the reaction was stirred at ambient temperature for 1 h under N2. The reaction was concentrated to dryness under reduced pressure to provide the title compound (10 mg, quantitative) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.62-7.57 (m, 2H), 7.47-7.34 (m, 6H), 7.03 (dd, J=8.5, 1.5 Hz, 1H), 6.29 (dd, J=7.5, 2.5 Hz, 1H), 6.12 (d, J=2.5 Hz, 1H), 5.18 (s, 2H), 4.55-4.43 (m, 2H), 3.72 (s, 3H), 3.38-3.14 (m, 12H), 2.14 (m, 4H); ESI MS m/z 483 [M+H]+; HPLC (Method A) 92.8% (AUC), tR=13.6 min.

Workup

  1. concentrationThe reaction was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1659f1d3c47b4d8ca59ae03bb085cd9f
Source dataset
uspto-grants-2016_03
Patent number
US09296743B2

Reaction notes

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