3-Amino-1-methyl-5-phenyl-1H-benzo[E][1,4]diazepin-2(3H)-one → N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-((R)1-phenylethyl)-urea

HRID 620629Notes

Reaction equation

HRID 620629 reaction equation
[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]([CH3:19])[C:3]1=[O:20].[CH3:21][C@@H:22]([N:29]=[C:30]=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[CH3:19][N:4]1[C:5]2[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=2[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:8][CH:2]([NH:1][C:30]([NH:29][C@@H:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:21])=[O:31])[C:3]1=[O:20]

Participants

4

Reactant 2

HCID 27296813-Amino-1-methyl-5-phenyl-1H-benzo[E][1,4]diazepin-2(3H)-oneHCID 7018262(R)-(+)-1-Phenylethyl isocyanate

Product 1

HCID 15637198N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-((R)1-phenylethyl)-urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Equimolar amounts of 3(R,S)-amino-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one and (R)-(+)-α-methylbenzylisocyanate were mixed in 8 ml of dry tetrahydrofuran at room temperature. The reaction mixture was allowed to stand for 8 hours and was then filtered. The collected solids were washed with tetrahydrofuran and dried in vacuo over P2O5 to give the analytical product as a mixture of diastereomers: m.p. 146°-150° C.

Workup

  1. filtrationwas then filtered
  2. washThe collected solids were washed with tetrahydrofuran
  3. dry with materialdried in vacuo over P2O5
  4. customto give the analytical product
  5. additionas a mixture of diastereomers

Sources & evidence

ORD record
ord-af868ba868bd448fa10483c07f013ccd
Source dataset
uspto-grants-1989_04
Patent number
US04820834

Reaction notes

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