Tetrahydrofuran → HCID 178520437, compound

HRID 1489523Notes

Reaction equation

HRID 1489523 reaction equation
[CH:1]1([CH2:7][CH2:8][C:9]([NH:11][CH:12]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:16]3[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=3[N:14](C)[C:13]2=S)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:32][OH:33].C(N(CC)CC)C.C1COCC1>CO>[CH:1]1([CH2:7][CH2:8][C:9]([NH:11][CH:12]2[C:13](=[N:32][OH:33])[NH:14][C:15]3[CH:28]=[CH:27][CH:26]=[CH:25][C:16]=3[C:17]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[N:18]2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 152287163-cyclohexyl-N-(2,3-dihydro-1-methyl-5-phenyl-2-thioxo-1H-1,4-benzodiazepin-3-yl)propanamide

Product 1

HCID 178520437HCID 178520437, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-cyclohexyl-N-(2,3-dihydro-1-methyl-5-phenyl-2-thioxo-1H-1,4-benzodiazepin-3-yl)propanamide (740 mg, 1.83 mmol), hydroxylamine hydrochloride (140 mg, 2 mmol) and triethylamine (280 μL, 203 mg, 2 mmol) in methanol (15 mL)/THF (15 mL) was stirred at room temperature for 3 h. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2 /MeOH (98:2). The residue recrystallized from ethyl acetate. The first isomer to crystallize was recrystallized from ethyl acetate to give (E)-3-cyclohexyl-N-(2,3-dihydro-2-hydroxyimino-5-phenyl-1H-1,4-benzodiazepin-3-yl)propanamide as a solid, m.p. 196° C.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by flash column chromatography on silica gel
  3. washeluting with CH2Cl2 /MeOH (98:2)
  4. customThe residue recrystallized from ethyl acetate
  5. customThe first isomer to crystallize
  6. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4f7c24c52e964d66852484b73663014a
Source dataset
uspto-grants-1997_10
Patent number
US05679672

Reaction notes

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