Diisopropylcarbodiimide → HCID 178487384, compound

HRID 272692Notes

Reaction equation

HRID 272692 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH:13]=[CH:14][C:15]3[C:21](=[O:22])[NH:20][C:19]4[CH:23]=[C:24]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH:25]=[CH:26][C:18]=4[NH:17][C:16]=3[CH:32]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].O[NH:34][C:35](=[NH:37])[CH3:36].CC(C)N=C=NC(C)C>CN(C=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH:13]=[CH:14][C:15]3[C:21](=[O:22])[NH:20][C:19]4[CH:23]=[C:24]([CH2:27][CH2:28][C:29]([O:31][NH:37][C:35](=[NH:34])[CH3:36])=[O:30])[CH:25]=[CH:26][C:18]=4[NH:17][C:16]=3[CH:32]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 692186873-[3-(3-Methoxy-4-nitrophenyl)-11-oxo-10,11-dihydro-5h-dibenzo[b,e][1,4]diazepin-8-yl]propanoic acidHCID 178465666HCID 178465666, compound

Product 1

HCID 178487384HCID 178487384, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 230 (65 mg, 0.15 mmol), N-hydroxy-acetamidine (14 mg, 0.18 mmol) in 1 mL of DMF was treated with DIC in 1 mL of CH2Cl2 at 0° C. The reaction mixture was stirred overnight and partitioned between EtOAc and water. The organic layer was separated, washed with brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 100:1 ethyl acetate/MeOH to provide the desired product. MS (DCI) m/e 490 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ 9.83 (s, 1H), 8.01 (d, J=8.29 Hz, 1H), 7.94 (s, 1H), 7.79 (d, J=8.29 Hz, 1H), 7.52 (d, J=1.23 Hz, 1H), 7.33-7.34 (m, 2H), 7.29 (m, 1H), 6.93 (m, 1H), 6.83-6.85 (m, 2H), 6.27 (s, 2H), 4.03 (s, 3H), 2.73-2.76 (m, 2H), 2.58-2.62 (m, 2H), 1.72 (s, 3H).

Workup

  1. custompartitioned between EtOAc and water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by flash column chromatography on silica gel with 100:1 ethyl acetate/MeOH

Sources & evidence

ORD record
ord-92e8efe772d446d1b0dc7b06749bb826
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

Loading…