Triethylamine → N-(7-chloro-2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-[4-(dimethylamino)-1-naphthalenyl]-urea

HRID 2223065Notes

Reaction equation

HRID 2223065 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](C(O)=O)=[CH:5][CH:4]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])C=CC=CC=1.C([N:36]([CH2:39]C)CC)C.[NH2:41][CH:42]1[N:48]=[C:47]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:46]2[CH:55]=[C:56]([Cl:59])[CH:57]=[CH:58][C:45]=2[N:44]([CH3:60])[C:43]1=[O:61]>C1(C)C=CC=CC=1>[Cl:59][C:56]1[CH:57]=[CH:58][C:45]2[N:44]([CH3:60])[C:43](=[O:61])[CH:42]([NH:41][C:39]([NH:36][C:6]3[C:7]4[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:3]([N:2]([CH3:1])[CH3:16])=[CH:4][CH:5]=3)=[O:24])[N:48]=[C:47]([C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)[C:46]=2[CH:55]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 5226954-(Dimethylamino)-1-naphthoic acidHCID 221352663-amino-7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one

Product 1

HCID 10239302N-(7-chloro-2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-[4-(dimethylamino)-1-naphthalenyl]-urea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

As illustrated in the scheme above, a mixture of 4-(dimethylamino)-1-naphthalenecarboxylic acid (0.1 mmol), diphenylphosphoryl azide (0.15 mmol) and triethylamine (0.3 mmol) in toluene (10 ml) was heated at reflux overnight. The solvent was evaporated in vacuo, and then the residue was redissolved in dichloroethane, added to INTERMEDIATE 1 (0.08 mmol) and heated at 70° C. for 4 hours. The solvent was evaporated in vacuo and the residue was taken in dichloromethane (50 ml). The organic phase was washed with brine (2×10 ml); the organic phase was dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with ether and the title compound was obtained as a colorless solid (9 mg, 22%); 1H-NMR (CDCl3): δ 8.27 (m, 1H), 8.11 (m, 1H), 7.60 (d, J=8 Hz, 1H), 7.77-7.29 (m, 10H), 7.08 (d, J=8.4 Hz, 1H), 6.75 (br s, 2H), 5.56 (d, J=8.4 Hz, 1H), 3.39 (s, 3H) and 2.90 (s, 6H); MS (ESI) (M+H)+=512.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe solvent was evaporated in vacuo
  4. dissolutionthe residue was redissolved in dichloroethane
  5. customThe solvent was evaporated in vacuo
  6. washThe organic phase was washed with brine (2×10 ml)
  7. dry with materialthe organic phase was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-cab4db57224a4b979dafdbd3f020383f
Source dataset
uspto-grants-2008_05
Patent number
US07375101B2

Reaction notes

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