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Hydrochloric Acid → HCID 67068023, compound

HRID 1037333
Notes
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Reaction equation

HRID 1037333 reaction equation
[CH3:1][N:2]1[C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[CH:4]=[N:3]1)[C:11](=[O:15])[C:10]([C:16]1[CH:17]=[CH:18][C:19]([C:22]2([NH:26]S(C(C)(C)C)=O)[CH2:25][CH2:24][CH2:23]2)=[N:20][CH:21]=1)=[C:9]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[O:8]3.[ClH:39].O1CCOCC1>CO>[ClH:39].[NH2:26][C:22]1([C:19]2[N:20]=[CH:21][C:16]([C:10]3[C:11](=[O:15])[C:12]4[C:7]([O:8][C:9]=3[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[C:6]3[N:2]([CH3:1])[N:3]=[CH:4][C:5]3=[CH:14][CH:13]=4)=[CH:17][CH:18]=2)[CH2:25][CH2:24][CH2:23]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 670678412-Methyl-propane-2-sulfinic acid {1-[5-(1-methyl-6-oxo-8-phenyl-1,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl)-pyridin-2-yl]-cyclobutyl}-amide

Product 1

HCID 67068023HCID 67068023, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

To a solution of 2-methyl-propane-2-sulfinic acid {1-[5-(1-methyl-6-oxo-8-phenyl-1,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl)-pyridin-2-yl]-cyclobutyl}-amide (34 mg, 0.0645 mmol) in MeOH (6 mL) was added a solution of HCl in dioxane (4 M, 0.32 mL, 1.28 mmol). The reaction mixture was stirred at RT for 30 min before evaporating to dryness. The resulting residue was dissolved in a mixture of MeOH (1 mL), water (4 mL) and then chromatographed on a 5 g C18 cartridge {gradient 20 to 60% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound (24.3 mg, 82%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.78 (br s, 3H), 8.41 (dd, J=2.2 and 0.8 Hz, 1H), 8.29 (s, 1H), 7.89-7.81 (m, 3H), 7.75 (d, J=8.3 Hz, 1H), 7.59-7.57 (m, 2H), 7.51-7.41 (m, 3H), 4.41 (s, 3H), 2.60-2.55 (m, 4H), 2.26-2.15 (m, 1H), 2.05-1.94 (m, 1H). LCMS (Method E): =3.22 min, [M+H]+=423.

Workup

  1. custombefore evaporating to dryness
  2. dissolutionThe resulting residue was dissolved in a mixture of MeOH (1 mL), water (4 mL)
  3. customchromatographed on a 5 g C18 cartridge {gradient 20 to 60% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)}

Sources & evidence

ORD record
ord-5df6d7a7f6694137bd126790c5f26e2a
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08546376B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes