Triethylamine → 1-(2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-benzyloxycarbonylphenyl)urea

HRID 1979482Notes

Reaction equation

C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.C([N:20]([CH2:23]C)CC)C.[C:25]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:35])[C:26]1[CH:34]=[CH:33][CH:32]=[C:28](C([O-])=O)[CH:27]=1.C(C(C[N:51]1[C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][C:56]=2[N:55]([CH:62]2[CH2:67][CH2:66][CH2:65][CH2:64][CH2:63]2)[CH2:54][CH:53]([NH2:68])[C:52]1=[O:69])=O)(C)(C)C>O1CCCC1>[O:69]=[C:52]1[NH:51][C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][C:56]=2[N:55]([CH:62]2[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67]2)[CH2:54][CH:53]1[NH:68][C:23]([NH:20][C:28]1[CH:32]=[CH:33][CH:34]=[C:26]([C:25]([O:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)=[O:35])[CH:27]=1)=[O:8]

Participants

Conditions

Temperature: 100 °C

Procedure

Diphenylphosphoryl azide (938 mg) and triethylamine (354 mg) were added to a solution of monobenzyl isophthalate (874 mg) in anhydrous tetrahydrofuran (30 ml), the mixture was stirred at 100° C. for one hour and 30 minutes. The resultant mixture was allowed to cool, 1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (680 mg) was added thereto, the mixture was stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3), to thereby obtain 890 mg of the title compound.

Workup

temperatureto cool
stirringthe mixture was stirred at room temperature for one hour
concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record: ord-d3a24068c3ab4c7899dd0dd5280dceac
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06239131B1

Reaction notes

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