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Hydrochloric Acid → HCID 178432276, compound

HRID 74480
Notes
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Reaction equation

HRID 74480 reaction equation
[F:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[NH:10][C:6]=2[CH:5]=[C:4]([NH2:12])[CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:23](=[N:36]N)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl>CN1CCOCC1>[C:23](=[N:36][NH:12][C:4]1[CH:3]=[C:2]([F:1])[C:7]2[NH:8][C:9]([CH3:11])=[N:10][C:6]=2[CH:5]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79304DiphenylmethylidenehydrazineHCID 2733832Lithium hexamethyldisilazaneHCID 680053077-fluoro-2-methyl-3H-benzimidazol-5-yl amine

Product 1

HCID 178432276HCID 178432276, compound

Reagents, catalysts & solvents 1

HCID 7972
4-Methylmorpholine
Solvent

Conditions

Temperature
100 °C

Procedure

In a separate reaction container, 7-fluoro-2-methyl-3H-benzimidazol-5-yl amine (100 mg, 0.44 mmol), lithium bis(trimethylsilyl) amide (190 mg, 1.1 mmol), and benzophenone hydrazone (94.3 mg, 0.48 mmol) were dissolved in N-methyl-morpholine (0.5 ml) under a nitrogen atmosphere. Then, the prepared solution containing the catalyst was added thereto. After deaeration, this was heated and stirred at 100° C. under a nitrogen atmosphere for two hours. The reaction mixture was cooled to room temperature, and then an aqueous solution of 6 M hydrochloric acid (0.5 ml) was added thereto. The organic layer was isolated, and concentrated under reduced pressure. Thus, crude N-benzhydrylidene-N′-(7-fluoro-2-methyl-1H-benzimidazol-5-yl)-hydrazine was obtained. The obtained crude product was used in subsequent reactions without being purified.

Workup

  1. additionThen, the prepared solution containing the catalyst
  2. additionwas added
  3. temperatureAfter deaeration, this was heated
  4. temperatureThe reaction mixture was cooled to room temperature
  5. customThe organic layer was isolated
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0522042ac78d4dc9b73fc28706cba004
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08829199B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes