Hydrochloric Acid → HCID 68658088, compound

HRID 930745Notes

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][NH:32][CH:31]([CH2:35][OH:36])[C:26]=4[N:27]3[CH3:30])=[CH:23][CH:22]=2)[C:17](=[O:37])[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][NH:32][CH:31]([CH2:35][OH:36])[C:26]=4[N:27]3[CH3:30])=[CH:23][CH:22]=2)[C:17](=[O:37])[CH:16]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A 1.0 M solution of HCl in Et2O (0.13 mL, 0.13 mmol) was added to a solution of 4-(benzyloxy)-1-(1-(hydroxymethyl)-9-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-7-yl)pyridin-2(1H)-one (55 mg, 0.13 mmol) in CH2Cl2 (10 mL) under N2 and stirred at 25° C. for 1 h. The solution was concentrated to afford the title compound (32 mg, 54%) as an off-white powder: mp 168-170° C.; 1H NMR (500 MHz, DMSO-d6) δ 9.48 (br s, 1H), 9.10 (br s, 1H), 7.56 (overlapping dd, J=8.5 Hz, 2H), 7.52 (s, 1H), 7.49-7.41 (m, 4H), 7.40-7.36 (m, 1H), 7.01 (dd, J=7.0, 1.5 Hz, 1H), 6.12 (dd, J=7.5, 1.5 Hz, 1H), 5.98 (d, J=1.5 Hz, 1H), 5.72 (t, J=3.3 Hz, 1H), 5.16 (s, 2H), 4.89-4.82 (m, 1H), 4.07-4.01 (m, 1H), 3.80-3.71 (m, 1H), 3.72 (s, 3H), 3.61-3.50 (m, 1H), 3.49-3.43 (m, 1H), 3.02-2.94 (m, 2H); ESI MS m/z 416 [M+H]+.

Workup

concentrationThe solution was concentrated

Sources & evidence

ORD record: ord-20f8e6bd678e49d381772cb6027683f1
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296743B2

Reaction notes

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