Methanol → 5-[3-(N-hydroxyamidino)phenyl]-1H-naphtho[1,2-b][1,4]diazepin-2,4(3H,5H)-dione

HRID 1622316Notes

Reaction equation

HRID 1622316 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]2C(=O)[CH2:14][C:13](=[O:17])[NH:12][C:11]3[C:18]4[C:23]([CH:24]=[CH:25][C:10]2=3)=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:6]=[CH:7][CH:8]=1)#[N:2].Cl.[NH2:27][OH:28].C(N(CC)CC)C.[CH3:36][OH:37]>C1COCC1>[OH:28][NH:27][C:1]([C:3]1[CH:4]=[C:5]([N:9]2[C:36](=[O:37])[CH2:14][C:13](=[O:17])[NH:12][C:11]3[C:18]4[C:23]([CH:24]=[CH:25][C:10]2=3)=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:6]=[CH:7][CH:8]=1)=[NH:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 468632195-(3-Cyanophenyl)-1H-naphtho[1,2-b][1,4]diazepin-2,4(3H,5H)-dione

Product 1

HCID 1785133085-[3-(N-hydroxyamidino)phenyl]-1H-naphtho[1,2-b][1,4]diazepin-2,4(3H,5H)-dioneYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(3-cyanophenyl)-1H-naphtho[1,2-b][1,4]diazepin-2,4(3H,5H)-dione (37 mg, 0.11 mmol), hydroxylamine hydrochloride (76 mg, 1.1 mmol) and triethylamine (0.16 mL, 1.1 mmol) in THF (0.65 mL)/methanol (1.3 mL) was heated under reflux for 2 hours. The solvent was removed under reduced pressure, and to the residue was added water (4 mL). The precipitated crystal was filtered and washed with water. The crystal was dried in vacuo at 50° C., to give the titled compound as a light gray crystal (36 mg, 91%).

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe solvent was removed under reduced pressure
  3. additionto the residue was added water (4 mL)
  4. filtrationThe precipitated crystal was filtered
  5. washwashed with water
  6. customThe crystal was dried in vacuo at 50° C.

Sources & evidence

ORD record
ord-d36a10281a974126980d4beb268f8313
Source dataset
uspto-grants-2014_07
Patent number
US08778933B2

Reaction notes

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