Dimethylformamide → HCID 86752407, compound

HRID 1599067Notes

Reaction equation

HRID 1599067 reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([N:13](C(C)C)C2C=CC(OC)=CC=2)=[O:12])[C:6]2[CH:25]=[CH:26][CH:27]=[CH:28][C:5]=2[N:4]([C:29]2[N:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[C:3]1=[O:35].[NH:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=[C:37]1[C:45]([OH:47])=O.ON1[C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][C:52]=2N=N1.Cl.CN(C)[CH2:61][CH2:62][CH2:63]N=C=NCC.CN([CH:73]=[O:74])C>C(OCC)(=O)C>[CH:62]([C:10]([C:56]1[CH:55]=[CH:54][C:53]([O:74][CH3:73])=[CH:52][CH:57]=1)([C:11](=[O:12])[NH2:13])[N:7]1[C:8](=[O:9])[CH:2]([NH:1][C:45]([C:37]2[NH:36][C:44]3[C:39]([CH:38]=2)=[CH:40][CH:41]=[CH:42][CH:43]=3)=[O:47])[C:3](=[O:35])[N:4]([C:29]2[N:30]=[CH:31][CH:32]=[CH:33][N:34]=2)[C:5]2[CH:28]=[CH:27][CH:26]=[CH:25][C:6]1=2)([CH3:63])[CH3:61]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 72899Indole-2-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 54424075HCID 54424075, compound

Product 1

HCID 86752407HCID 86752407, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(3-Amino-2,4-dioxo-5-pyrimidin-2-yl-2,3,4,5-tetrahydro-benzo [b] [1,4]diazepine-1-yl)-N-isopropyl-N-(4-methoxy-phenyl)-acetamide (933 mg, 1.97 mmol) in DMF (20 mL) were added indole-2-carboxylic acid (333 mg, 2.07 mmol), N-hydroxybenzotriazole (266 mg, 1.97 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (415 mg, 2.16 mmol) successively with stirring at ambient temperature. The resultant mixture was stirred at ambient temperature for 18 hours. The solvent was evaporated under reduced pressure to give a yellow oil which was dissolved in ethyl acetate (100 mL), washed with water (2×30 mL), dried over MgSO4, filtered and concentrated under reduced pressure to a give a tan foam. The crude product was purified by flash chromatography on silica gel (30 g) eluting with ethyl acetate (600 mL). Appropriate fractions were combined and concentrated in vacuo to give the title compound (902 mg, 1.46 mmol) as a white foam: 1H NMR (CDCl3, 400 MHz): 9.44 (s 1H), 8.75 (d, 2H, J=4.4 Hz), 7.64-6.88 (m,15H), 5.60 (d, 1H, J=6.8 Hz), 5.03 (m, 1H), 4.45 (d, 1H, J=16.6 Hz), 3.99 (d, 1H, J=16.6 Hz), 3.81 (s, 3H), 1.07 (m, 6H); TLC (CH2Cl2 /CH3OH (19:1)): Rf =0.63; MS (FAB) m/z 618.2 (MH+).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customto give a yellow oil which
  3. washwashed with water (2×30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to
  7. customa give a tan foam
  8. customThe crude product was purified by flash chromatography on silica gel (30 g)
  9. washeluting with ethyl acetate (600 mL)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-47eea2bb7ae24ad389cf6ad9b09b38d4
Source dataset
uspto-grants-1998_04
Patent number
US05739129

Reaction notes

Loading…