Hydrochloric Acid → HCID 70124992, compound

HRID 1596377Notes

Reaction equation

HRID 1596377 reaction equation
[NH2:1][CH:2]1[N:8]=[C:7]([CH3:9])[C:6]2[CH:10]=[CH:11][CH:12]=[C:13]([N:14]([CH3:16])[CH3:15])[C:5]=2[N:4]([CH2:17][C:18]([N:20]2[CH2:26][CH:25]3[CH2:27][CH2:28][CH:22]([CH2:23][CH2:24]3)[CH2:21]2)=[O:19])[C:3]1=[O:29].[C:30]1([CH3:39])[CH:35]=[CH:34][CH:33]=[C:32]([N:36]=[C:37]=[O:38])[CH:31]=1.[ClH:40]>O1CCCC1.C(OCC)(=O)C>[ClH:40].[CH:25]12[CH2:24][CH2:23][CH:22]([CH2:28][CH2:27]1)[CH2:21][N:20]([C:18]([CH2:17][N:4]1[C:5]3[C:13]([N:14]([CH3:16])[CH3:15])=[CH:12][CH:11]=[CH:10][C:6]=3[C:7]([CH3:9])=[N:8][CH:2]([NH:1][C:37]([NH:36][C:32]3[CH:33]=[CH:34][CH:35]=[C:30]([CH3:39])[CH:31]=3)=[O:38])[C:3]1=[O:29])=[O:19])[CH2:26]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 69303m-Tolyl isocyanateHCID 54200208HCID 54200208, compound

Product 1

HCID 70124992HCID 70124992, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (3RS)-3-amino-1-[(3-azabicyclo[3.2.2]non-3-yl)-carbonylmethyl]-5-methyl-9-(N,N-dimethylamino)-2,3-dihydro-1H-1,4-benzodiazepin-2-one (285 mg) in tetrahydrofuran (4 ml) was added dropwise 3-tolyl isocyanate (100 mg) under stirring at room temperature. The mixture was stirred at room temperature for 2 hours. Removal of the solvent in vacuo afforded a residue, which was triturated in diisopropyl ether and collected by filtration to give a white powder. To a solution of the powder in ethyl acetate was added 4N-hydrogen chloride in ethyl acetate (0.25 ml) under cooling. The mixture was evaporated in vacuo to dryness. The residue was washed with diisopropyl ether and collected by filtration to afford N-[(3RS)-1-(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl-5-methyl-9-(N,N-dimethylamino )-2,3-dihydro-2-oxo-1H-1,4-benzodiazepin-3-yl]-N′-(3-methylphenyl)urea hydrochloride (250 mg,61.5%) as a crystalline powder.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. customRemoval of the solvent in vacuo
  3. customafforded a residue, which
  4. customwas triturated in diisopropyl ether
  5. filtrationcollected by filtration
  6. customto give a white powder
  7. temperatureunder cooling
  8. customThe mixture was evaporated in vacuo to dryness
  9. washThe residue was washed with diisopropyl ether
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-69307150696545f8b359116e8101f624
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

Loading…