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Methanol → HCID 58190476, compound

HRID 1892410
Notes
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Reaction equation

HRID 1892410 reaction equation
O=[C:2]1[C:10]2C(=CC=CC=2)C(=O)[N:3]1[O:12][CH2:13][C:14]([NH2:16])=[O:15].O.NN.CO.[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>C(O)(=O)C>[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:2](=[N:3]/[O:12][CH2:13][C:14]([NH2:16])=[O:15])/[CH3:10])[CH:40]=[CH:41][C:36]4=[N:35][N:34]=3)=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 140744182-[(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]acetamide2×HCID 581904611-(3-(Quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

Product 1

HCID 58190476HCID 58190476, compound

Reagents, catalysts & solvents 1

HCID 176
Acetic Acid
Solvent

Conditions

Temperature
95 °C

Procedure

A microwave tube was charged with 2-(1,3-dioxoisoindolin-2-yloxy)acetamide (intermediate V) (166 mg, 0.76 mmol), hydrazine monohydrate (34.4 mg, 0.69 mmol) and 2 mL of methanol. It was heated at 95° C. for 12 h under microwave irradiation. After cooling, solid was removed by filtration and the solution was concentrated under reduced pressure. The residue was diluted with methanol, then 1-(3-(quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (41.2) (32 mg, 0.105 mmol) and 0.3 mL of acetic acid were added and the mixture was stirred at 40° C. overnight. After concentration, the residue was purified by prep-HPLC to afford the title compound. 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.86 (dd, 1H), 8.33-8.27 (m, 2H), 7.98-7.95 (m, 2H), 7.78 (dd, 1H), 7.69 (d, 1H), 7.50 (dd, 1H), 7.31 (d, 2H), 4.77 (s, 2H), 4.63 (s, 2H), 2.32 (s, 3H). LCMS (method A): [MH]+=376, tR=4.02 min.

Workup

  1. temperatureAfter cooling
  2. customsolid was removed by filtration
  3. concentrationthe solution was concentrated under reduced pressure
  4. additionThe residue was diluted with methanol
  5. concentrationAfter concentration
  6. customthe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-2f8cfdcbaaf74db48974029e9110f9d2
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08507676B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes