Aniline → HCID 67699525, compound

HRID 343200Notes

Reaction equation

HRID 343200 reaction equation
C([C:4](C1C=CC=CC=1)([C:31](=[O:33])[NH2:32])[N:5]1[C:11](=[O:12])[C:10]([CH:14]([CH2:18][CH3:19])C(O)=O)([CH3:13])[C:9](=[O:20])[N:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:7]2[CH:27]=[CH:28][CH:29]=[CH:30][C:6]1=2)(C)C.F[P-](F)(F)(F)(F)F.[N:47]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][C:50]=2N=N1.[CH:67]1[CH:68]=[CH:69][C:70]2N(O)N=N[C:71]=2[CH:72]=1.N[C:78]1[CH:83]=CC=C[CH:79]=1.CN([CH:87]=[O:88])C>CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH:78]([N:32]([C:72]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)[C:31](=[O:33])[CH2:4][N:5]1[C:11](=[O:12])[C:10]([CH2:14][CH2:18][CH2:19][C:87](=[O:88])[NH:47][C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:50]=2)([CH3:13])[C:9](=[O:20])[N:8]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:7]2[CH:27]=[CH:28][CH:29]=[CH:30][C:6]1=2)([CH3:83])[CH3:79]

Participants

8

Reactant 5

HCID 6115AnilineHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67700610HCID 67700610, compound

Product 1

HCID 67699525HCID 67699525, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 95 mg of [1-(Isopropyl-phenyl-carbamoylmethyl)-3-methyl-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-butyric acid, prepared as in Intermediate 34, 75.1 mg of BOP, 24.2 mg of HOBT, 21 mg of DMAP and 16.4 mg of aniline in DMF (0.5 ml) is stirred at RT overnight. The reaction mixture is diluted with 50 mL of ethyl acetate and washed with 1N aqueous sodium hydroxide solution (×2), water, 0.5N hydrochloric acid (×2), water and brine. The organic extract is dried over MgSO4 and concentrated in vacuo to afford the crude product. Purification by silica gel flash column chromatography (10% MeOH in methylene chloride) gave 45 mg of the title compound as a clear glass: 1H NMR (300 MHz, CDCl3) δ8.6 (s, 1H), 6.8-7.7 (m, 19H), 5.11 (sept, 1H, J=7.1), 4.59 (d, 1H, J=8.9), 3.71 (d, 1H, J=8.9,), 2.09 (m, 2H), 1.81 (m, 2H), 1.59 (s, 3H), 1.4 (m, 2H), 1.04 (dd, 6H, J=7.1); low resolution MS (FAB) m/e 603 (MH+).

Workup

  1. washwashed with 1N aqueous sodium hydroxide solution (×2), water, 0.5N hydrochloric acid (×2), water and brine
  2. extractionThe organic extract
  3. dry with materialis dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto afford the crude product
  6. customPurification by silica gel flash column chromatography (10% MeOH in methylene chloride)

Sources & evidence

ORD record
ord-539f49e6a7124fba90efb8f83559e232
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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