Methanesulfonic acid, aminoimino- → HCID 178481554, compound

HRID 1653863Notes

Reaction equation

HRID 1653863 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][N:9]1[C:15]2[CH:16]=[CH:17][C:18]([C:20]#[C:21][CH2:22][CH2:23][CH2:24][NH2:25])=[CH:19][C:14]=2[C:13](=[O:26])[N:12]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH2:11][C:10]1=[O:32].[C:33](S(O)(=O)=O)([NH2:35])=[NH:34]>C(=O)(O)[O-].[K+]>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][N:9]1[C:15]2[CH:16]=[CH:17][C:18]([C:20]#[C:21][CH2:22][CH2:23][CH2:24][NH:25][C:33]([NH2:35])=[NH:34])=[CH:19][C:14]=2[C:13](=[O:26])[N:12]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH2:11][C:10]1=[O:32]

Participants

4

Reactant 2

HCID 9877361Methanesulfonic acid, aminoimino-HCID 229051171-methyl-4-(2-carboxyethyl)-7-(5-amino-1-pentynyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione trifluoracetate

Product 1

HCID 178481554HCID 178481554, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 516893Potassium BicarbonateSolvent

Procedure

To a magnetically stirred solution of 6 mgs of 1-methyl-4-(2-carboxyethyl)-7-(5-amino-1-pentynyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione trifluroacetate (0.017 mmol) in 1.0 mL 10% potassium bicarbonate was added 31.0 mgs of formamidine sulfonic acid (0.25 mmol). After 30 minutes, the reaction mixture was quenched with 0.5 mL acetic acid and concentrated in vacuo. The resulting residue was diluted with 2 mL water and purified by high pressure liquid chromatography, using a 1/2" C-18 reverse-phase column, eluting with a solvent gradient of 10:90 methanol(0.1% trifluroacetic acid)/water (0.1% trifluroacetic acid), time 0 to 10 min, to 50:50 methanol(0.1% trifluroacetic acid)/water (0.1% trifluroacetic acid), time 10 min to 40 min, flow=10 ml/min (Rt =36.8 min, un detection 254 nm) to yield 4.5 mgs (67%) 1-methyl-4-(2-carboxyethyl)-7-(5-guanidino- 1-pentynyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione trifluroacetate. HRMS (FAB) molecular ion m/z=386.1823 (cald. C19H24N5O4, 386.1829). 1H NMR (D2O) 7.60 (1H, d, 4JHH, Ar-H o-CON), 7.51 (1H, dd, 4JHH =2 Hz, 3JHH =8 Hz, Ar-H p-CON), 7.20 (1H, d, 3JHH =8 Hz, Ar-H m-CON), 4.05 (1H, d, 2JHH =14 Hz, NCHHCO), 3.92 (1H, m, NCHHCH2), 3.72 (1H, d, 2JHH =14 Hz, NCHHCO), 3.40 (1H, m, NCHHCH2), 3.23-3.15 (5H, NCH3, H2NC(=NH2)NHCH2), 2.58 (2H, m, CH2CO2), 2.38 (2H, t, 3JHH =7 Hz, C∫CCH2), 1.76 (2H, p, 3JHH =7 Hz, CH2CH2CH2).

Workup

  1. customthe reaction mixture was quenched with 0.5 mL acetic acid
  2. concentrationconcentrated in vacuo
  3. additionThe resulting residue was diluted with 2 mL water
  4. custompurified by high pressure liquid chromatography
  5. washeluting with a solvent gradient of 10:90 methanol(0.1% trifluroacetic acid)/water (0.1% trifluroacetic acid), time 0 to 10 min, to 50:50 methanol(0.1% trifluroacetic acid)/water (0.1% trifluroacetic acid), time 10 min to 40 min, flow=10 ml/min (Rt =36.8 min, un detection 254 nm)

Sources & evidence

ORD record
ord-75c2f0cbaea6410eb2593d375272e266
Source dataset
uspto-grants-1995_04
Patent number
US05403836

Reaction notes

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