7,12-Dimethylbenz(a)anthracene → HCID 18463921, compound

HRID 2231079Notes

Reaction equation

HRID 2231079 reaction equation
C([O:4][C:5]1[C:43]([Cl:44])=[CH:42][C:8]([C:9]([NH:11][CH:12]2[CH2:18][CH2:17][C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH3:22])[N:14]([CH2:23][C:24](=[O:40])[NH:25][CH:26]3[CH2:30][C:29](=[O:31])[O:28][CH:27]3[O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:13]2=[O:41])=[O:10])=[CH:7][C:6]=1[Cl:45])C=C.CC1C2C(=CC=CC=2)C(C)=C2C=1C=CC1C2=CC=CC=1>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:33]([O:32][CH:27]1[CH:26]([NH:25][C:24]([CH2:23][N:14]2[C:13](=[O:41])[CH:12]([NH:11][C:9](=[O:10])[C:8]3[CH:42]=[C:43]([Cl:44])[C:5]([OH:4])=[C:6]([Cl:45])[CH:7]=3)[CH2:18][CH2:17][C:16](=[O:19])[N:15]2[CH2:20][CH2:21][CH3:22])=[O:40])[CH2:30][C:29](=[O:31])[O:28]1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

5

Reactant 2

HCID 60017,12-Dimethylbenz(a)anthraceneHCID 18463939HCID 18463939, compound

Product 1

HCID 18463921HCID 18463921, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-allyloxy-N-{2-[(2-benzyloxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-methyl]-3,7-dioxo-1-propyl-[1,2]diazepan-4-yl}-3,5-dichloro-benzamide (10c, diastereomers) (103 mg, 0.16 mmol) in dichloromethane (15 mL) was added DMBA followed by Pd(PPh3)4 (30 mg, 0.026 mmol), stirred at room temperature for 7 hours. The reaction mixture was washed with water, dried over anhydrous Na2SO4, filtered and purified by flash chromatography using dichloromethane/methanol (99.5/0.5 to 97/3) to afford both anti diastereomer (18 mg, 18% yield, lower Rf) and syn diastereomer (48 mg, 50% yield, higher Rf) of the title compound. 1H-NMR (500 MHz, CDCl3) for the anti diastereomer: δ 0.9-1.02 (m, 3H), 1.65-185 (m, 2H), 2.01-2.18 (m, 0.5H), 2.20-2.30 (d, 0.5H), 2.37-2.47 (m, 1H), 2.58-2.70 (m, 1H), 2.90-3.00 (m, 1H), 3.00-3.10 (m, 1H), 3.25-3.50 (m, 1H), 4.0-4.15 (m, 2H), 4.15-4.25 (d, 1H), 4.40-4.55 (m, 1H), 4.55-4.67 (m, 1H), 4.72-4.82 (d, 1H), 5.05-5.17 (m, 1H), 5.27-5.38 (m, 2H), 6.90-7.00 (d, 1H), 7.25-7.40 (m, 6H), 7.60-7.70 (m, 1H), 7.80 (s, 2H; for the syn diastereomer: δ 0.9-1.00 (m, 3H), 1.50-1.70 (m, 2H), 1.8-1.92 (m, 1H), 2.38-2.42 (m, 1H), 2.48-2.58 (m, 1H), 2.74-2.87 (m, 1H), 2.88-2.98 (m, 1H), 3.00-3.13 (m, 1H), 3.17-3.30 (m, 1H), 4.00-4.12 (m, 1H), 4.14-4.30 (d, 1H), 4.22-4.32 (m, 1H), 4.62-4.46 (d, 1H), 4.75-4.80 (m, 1H), 4.90-4.95 (d, 1H), 5.10-5.20 (m, 1H), 5.53-5.57 (d, 1H), 6.24 (s, 1H), 6.49 (d, 1H), 6.70 (d, 1H), 7.25-7.40 (m, 5H), 7.71 (s, 2H). Analytical HPLC: 8.55 min for syn diastereomer and 8.57 min for the anti diastereomer. LC-MS (ES+) for the mixture of the product: m/e=621, 623 (M+H+).

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-722fa208f5134bc6b32c785f1a8f571f
Source dataset
uspto-grants-2002_07
Patent number
US06426413B1

Reaction notes

Loading…