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Hydrochloric Acid → HCID 58190473, compound

HRID 1892384
Notes
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Reaction equation

HRID 1892384 reaction equation
O.NN.[O:4]([N:11]1C(=O)C2[C:13](=CC=CC=2)[C:12]1=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N:22]1[C:31]2[C:26](=[CH:27][C:28]([CH2:32][C:33]3[N:37]4[N:38]=[C:39](C(=O)C)[CH:40]=[CH:41][C:36]4=[N:35][N:34]=3)=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1.Cl>CO>[C:5]1([O:4]/[N:11]=[C:12](/[C:39]2[CH:40]=[CH:41][C:36]3[N:37]([C:33]([CH2:32][C:28]4[CH:27]=[C:26]5[C:31](=[CH:30][CH:29]=4)[N:22]=[CH:23][CH:24]=[CH:25]5)=[N:34][N:35]=3)[N:38]=2)\[CH3:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 3560555N-phenoxyphthalimideHCID 581904611-(3-(Quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

Product 1

HCID 58190473HCID 58190473, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

Hydrazine monohydrate (5.45 mg, 0.109 mmol) was added to a solution of 2-phenoxyisoindoline-1,3-dione (Organic Lett, 2001, 31, 139) (30.8 mg, 0.129 mmol) in 10 mL of MeOH. The solution was heated at reflux for 2 h and then cooled to rt. White precipitate was filtered off and 1-(3-(quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (41.2) (30 mg, 0.1 mmol) was added. The pH value of solution was adjusted to 5-6 with 1N HCl solution. The reaction solution was then stirred at it overnight. Solvent was evaporated and the crude was purified by HPLC (acidic with 0.05% TFA) to give 23 mg (59%) of the title compound as a white solid (TFA salt). 1H-NMR (400 MHz, CDCl3) δ ppm 9.23 (d, 1H), 8.68 (d, 1H), 8.53 (d, 1H), 8.15 (m, 3H), 8.04 d, 1H), 7.83 (m, 1H), 7.40 (t, 2H), 7.29 (m, 2H), 7.15 (t, 1H), 4.92 (s, 2H), 2.56 (s, 3H). LC-MS (method H): [MH]+=395.2, tR=2.42 min.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 2 h
  3. filtrationWhite precipitate was filtered off
  4. customSolvent was evaporated
  5. customthe crude was purified by HPLC (acidic with 0.05% TFA)

Sources & evidence

ORD record
ord-bdadecdff2de4e88b150d97779dcc48a
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08507676B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes