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

HRID 474956
Notes
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Reaction equation

HRID 474956 reaction equation
[ClH:1].[CH3:2][N:3]1[C:11]2[CH:10]=[C:9]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([O:19][CH2:20][C:21]4[CH:22]=[N:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=4)[CH:14]=[N:13]3)[CH:8]=[CH:7][C:6]=2[C:5]2[CH2:31][N:32](C(OC(C)(C)C)=O)[CH2:33][CH2:34][CH2:35][C:4]1=2>CO>[ClH:1].[CH3:2][N:3]1[C:11]2[CH:10]=[C:9]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([O:19][CH2:20][C:21]4[CH:22]=[N:23][C:24]([C:27]([F:29])([F:30])[F:28])=[CH:25][CH:26]=4)[CH:14]=[N:13]3)[CH:8]=[CH:7][C:6]=2[C:5]2[CH2:31][NH:32][CH2:33][CH2:34][CH2:35][C:4]1=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66873698tert-butyl 6-methyl-8-(6-oxo-4-((6-(trifluoromethyl)pyridin-3-yl)methoxy)pyridazin-1(6H)-yl)-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate

Product 1

HCID 668731582-(6-Methyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indol-8-yl)-5-((6-(trifluoromethyl)pyridin-3-yl)methoxy)pyridazin-3(2H)-one hydrochlorideYield 61%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

1.25 M HCl in MeOH (4.0 mL) was added to tert-butyl 6-methyl-8-(6-oxo-4-((6-(trifluoromethyl)pyridin-3-yl)methoxy)pyridazin-1(6H)-yl)-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate (43 mg, 0.075 mmol), and the resulting solution was stirred under N2 at ambient temperature for 18 h. The solution was concentrated under reduced pressure, and the resulting residue was diluted with MeOH (1.0 mL) and Et2O (10 mL). The resulting solids were collected by filtration to provide the title compound (23 mg, 61%) as an off-white solid: 1H NMR (500 MHz, DMSO-d6) δ 8.91 (d, J=1.5 Hz, 1H), 8.87 (s, 2H), 8.22 (dd, J=8.5, 1.5 Hz, 1H), 8.02-8.00 (m, 2H), 7.64 (d, J=8.5 Hz, 1H), 7.57 (d, J=1.5 Hz, 1H), 7.13 (dd, J=8.5, 2.0 Hz, 1H), 6.56 (d, J=3.0 Hz, 1H), 5.41 (s, 2H), 4.44 (s, 2H), 3.72 (s, 3H), 3.47-3.43 (m, 2H), 3.10 (t, J=5.5 Hz, 2H), 2.08-2.04 (m, 2H); ESI MS m/z 470 [M+H]+; HPLC (Method A)>99% (AUC), tR=14.1 min.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionthe resulting residue was diluted with MeOH (1.0 mL) and Et2O (10 mL)
  3. filtrationThe resulting solids were collected by filtration

Sources & evidence

ORD record
ord-b853059c44c5416d9e2680dd78f28cf7
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08637501B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes