Hydrochloric Acid → 1-(6-Methyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indol-8-yl)-4-(6-methylpyridin-3-yl)pyridin-2(1H)-one hydrochloride

HRID 474919Notes

Reaction equation

HRID 474919 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]([N:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:18]=[N:19][C:20]([CH3:23])=[CH:21][CH:22]=4)=[CH:13][C:12]3=[O:24])[CH:7]=[CH:6][C:5]=2[C:4]2[CH2:25][N:26](C(OC(C)(C)C)=O)[CH2:27][CH2:28][CH2:29][C:3]1=2.[ClH:37]>CO>[ClH:37].[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]([N:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:18]=[N:19][C:20]([CH3:23])=[CH:21][CH:22]=4)=[CH:13][C:12]3=[O:24])[CH:7]=[CH:6][C:5]=2[C:4]2[CH2:25][NH:26][CH2:27][CH2:28][CH2:29][C:3]1=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70805194tert-Butyl 6-methyl-8-(4-(6-methylpyridin-3-yl)-2-oxopyridin-1(2H)-yl)-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate

Product 1

HCID 668737341-(6-Methyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indol-8-yl)-4-(6-methylpyridin-3-yl)pyridin-2(1H)-one hydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 6-methyl-8-(4-(6-methylpyridin-3-yl)-2-oxopyridin-1(2H)-yl)-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate (50 mg, 0.10 mmol) was treated with 1.25 M HCl in MeOH (6.0 mL), and the resulting solution was stirred at ambient temperature for 36 h. The solution was partially concentrated under reduced pressure and diluted with Et2O. The resulting solids were collected by filtration and washed with 99:1 CH2Cl2/MeOH to provide the title compound (37 mg, 85%) as a tan solid: mp 245-250° C. decomp.; 1H NMR (500 MHz, DMSO-d6) δ 9.10 (br s, 2H), 9.04 (s, 1H), 8.44 (s, 1H), 7.82 (d, J=7.0 Hz, 1H), 7.70-7.68 (m, 2H), 7.58 (s, 1H), 7.09 (d, J=8.0 Hz, 1H), 6.96 (s, 1H), 6.79 (d, J=7.0 Hz, 1H), 4.45. (s, 2H), 3.74 (s, 3H), 3.45-3.44 (m, 2H), 3.11-3.09 (m, 2H), 2.66 (s, 3H), 2.08-2.07 (m, 2H); ESI MS m/z 385 [M+H]+; HPLC (Method A) 97.9% (AUC), tR=8.9 min.

Workup

  1. concentrationThe solution was partially concentrated under reduced pressure
  2. additiondiluted with Et2O
  3. filtrationThe resulting solids were collected by filtration
  4. washwashed with 99:1 CH2Cl2/MeOH

Sources & evidence

ORD record
ord-eb1e44639d3148ebb1356e46d670914e
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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