HCID 22905128, compound → HCID 178481553, compound

HRID 865331Notes

Reaction equation

HRID 865331 reaction equation
CN1C2C=CC(CCCCCN)=CC=2C(=O)N(CCC(O)=O)CC1=O.FC(F)(F)C(O)=O.[CH3:33][N:34]1[C:40]2[CH:41]=[CH:42][C:43]([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][NH:50][C:51]([NH2:53])=[NH:52])=[CH:44][C:39]=2[C:38](=[O:54])[N:37]([CH2:55][CH2:56][C:57]([OH:59])=[O:58])[CH2:36][C:35]1=[O:60]>>[CH3:33][N:34]1[C:40]2[CH:41]=[CH:42][C:43]([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][NH:50][C:51]([NH2:53])=[NH:52])=[CH:44][C:39]=2[C:38](=[O:54])[N:37]([CH2:55][CH2:56][C:57]([OH:59])=[O:58])[CH2:36][C:35]1=[O:60]

Participants

3

Reactant 2

HCID 22905128HCID 22905128, compoundHCID 178481555HCID 178481555, compound

Product 1

HCID 178481553HCID 178481553, compound

Procedure

1-methyl-4-(2-carboxyethyl)-7-(5-guanidino-1-pentyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione was prepared by the method described in Example 2. Thus, 18 mgs 1-methyl-4-(2-carboxyethyl)-7-(5-amino-1-pentyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione ylelded 17 mgs (87%) 1-methyl-4-(2-carboxyethyl)-7-(5-guanidino-1-pentyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione trifluoracetate (1/2" C-18 reverse-phase column, eluting with a solvent gradient of 10:90 methanol(0.1% trifluoracetic acid)/water (0.1% trifluoracetic acid), time 0 to 10 min, to 50:50 methanol(0.1% trifluoracetic acid)/water (0.1% trifluoracetic acid), time 10 min to 40 min, flow=10 ml/min, Rt =38.5 min, un detection 254 nm). HRMS (FAB) molecular ion m/z=390.2132 (cald. C19H27N5O4, 390.2182)

Workup

  1. washeluting with a solvent gradient of 10:90 methanol(0.1% trifluoracetic acid)/water (0.1% trifluoracetic acid), time 0 to 10 min, to 50:50 methanol(0.1% trifluoracetic acid)/water (0.1% trifluoracetic acid), time 10 min to 40 min, flow=10 ml/min, Rt =38.5 min, un detection 254 nm)

Sources & evidence

ORD record
ord-eba5135338934029966f188bcb1b4b7b
Source dataset
uspto-grants-1996_10
Patent number
US05565449

Reaction notes

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