Hydrochloric Acid → 1-(1,2,3,4,5,6-Hexahydroazepino[4,3-b]indol-8-yl)-4-(6-(trifluoromethyl)pyridazin-3-yl)pyridin-2(1H)-one hydrochloride

HRID 474929Notes

Reaction equation

HRID 474929 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([C:8]2[N:9]=[N:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=2)[CH:5]=[CH:4][N:3]1[C:18]1[CH:19]=[CH:20][C:21]2[C:22]3[CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28][CH2:27][C:23]=3[NH:24][C:25]=2[CH:26]=1.[ClH:39]>CO.CCOCC>[ClH:39].[CH2:31]1[C:22]2[C:21]3[CH:20]=[CH:19][C:18]([N:3]4[CH:4]=[CH:5][C:6]([C:8]5[N:9]=[N:10][C:11]([C:14]([F:15])([F:17])[F:16])=[CH:12][CH:13]=5)=[CH:7][C:2]4=[O:1])=[CH:26][C:25]=3[NH:24][C:23]=2[CH2:27][CH2:28][CH2:29][NH:30]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66874312tert-butyl 8-(2-oxo-4-(6-(trifluoromethyl)pyridazin-3-yl)pyridin-1(2H)-yl)-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate

Product 1

HCID 668734101-(1,2,3,4,5,6-Hexahydroazepino[4,3-b]indol-8-yl)-4-(6-(trifluoromethyl)pyridazin-3-yl)pyridin-2(1H)-one hydrochlorideYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

tert-Butyl 8-(2-oxo-4-(6-(trifluoromethyl)pyridazin-3-yl)pyridin-1(2H)-yl)-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate (54 mg, 0.10 mmol) was treated with 1.25 M HCl in MeOH (9.9 mL), and the resulting solution was stirred at ambient temperature for 18 h. The solution was diluted with Et2O. The resulting solids were collected by filtration, washed with Et2O and dried to yield the title compound (33 mg, 70%) as a yellow powder: mp 310-315° C. decomp.; 1H NMR (500 MHz, DMSO-d6) δ 11.54 (s, 1H), 8.90 (s, 2H), 8.70 (d, J=9.0 Hz, 1H), 8.46 (d, J=9.0 Hz, 1H), 7.89 (d, J=7.5 Hz, 1H), 7.69 (d, J=8.5 Hz, 1H), 7.43 (d, J=1.5 Hz, 1H), 7.36 (d, J=2.0 Hz, 1H), 7.16 (dd, J=7.0, 2.0 Hz, 1H), 7.08 (dd, J=8.5, 2.0 Hz, 1H), 4.44 (s, 2H), 3.48-3.46 (m, 2H), 3.05 (t, J=5.5 Hz, 2H), 2.03-2.01 (m, 2H); ESI MS m/z 426 [M+H]+; HPLC (Method A) 97.3% (AUC), tR=12.3 min.

Workup

  1. filtrationThe resulting solids were collected by filtration
  2. washwashed with Et2O
  3. customdried

Sources & evidence

ORD record
ord-e7781950bddd49e9aba697e08d93f433
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

Loading…