Dichloromethane → HCID 59704203, compound

HRID 2427482Notes

Reaction equation

HRID 2427482 reaction equation
[NH2:1][C:2]1[O:3][C:4]2[C:9]([C@@H:10]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([Br:24])[CH:15]=3)[C:11]=1[C:12]#[N:13])=[CH:8][CH:7]=[C:6]([NH:25][C:26]([C@@H:28]([NH:30]C(=O)OCC1C3C=CC=CC=3C3C1=CC=CC=3)[CH3:29])=[O:27])[C:5]=2[NH2:48].C(Cl)Cl.[OH-].[Na+]>CO>[NH2:30][C@@H:28]([CH3:29])[C:26]([NH:25][C:6]1[C:5]([NH2:48])=[C:4]2[C:9]([C@@H:10]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([Br:24])[CH:15]=3)[C:11]([C:12]#[N:13])=[C:2]([NH2:1])[O:3]2)=[CH:8][CH:7]=1)=[O:27]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 59704208HCID 59704208, compound

Product 1

HCID 59704203HCID 59704203, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an oven-dried one-neck round bottom reaction flask charged with a magnetic stir bar at room temperature under argon was added (9H-fluoren-9-yl)methyl(S)-1-((R)-2,8-diamino-3-cyano-4-(3-bromo-4,5-dimethoxyphenyl)-4H-chromen-7-ylcarbamoyl)-ethylcarbamate (0.045 g, 0.063 mmol), CH2Cl2:MeOH, 1:1 (2.11 mL) and 2N NaOH (0.063 mL, 0.13 mmol). The orange suspension was stirred at room temperature overnight. The suspension was concentrated leaving a brown residue. The residue was extracted with CHCl3 (3×40 mL), dried over MgSO4, filtered and concentrated to give the crude product. Purification by flash column chromatography (silica gel 4 g pre-packed column, elution with CH2Cl2:MeOH, 1:1) gave 0.005 g (16%) of the title compound as a yellow solid: 1H-NMR (DMSO-d6): δ 8.32 (s, 1H), 7.02 (d, J=8.2 Hz, 1H), 6.98 (d, J=1.9 Hz, 1H), 6.91 (br s, 2H), 6.86 (d, J=1.9 Hz, 1H), 6.33 (d, J=8.5 Hz, 1H), 4.78 (br s, 2H), 4.69 (s, 1H), 3.80 (s, 3H), 3.70 (s, 3H), 1.22 (d, J=6.9 Hz, 3H). ESI-MS (C21H22BrN5O4) 487.09 m/z (%): 488 [M+H]+ (100%), 490 [M+H]+ (90%).

Workup

  1. additionTo an oven-dried one-neck round bottom reaction flask charged with a magnetic stir bar at room temperature under argon
  2. concentrationThe suspension was concentrated
  3. customleaving a brown residue
  4. extractionThe residue was extracted with CHCl3 (3×40 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product
  9. customPurification
  10. washby flash column chromatography (silica gel 4 g pre-packed column, elution with CH2Cl2:MeOH, 1:1)

Sources & evidence

ORD record
ord-c69ba0a6db574d7b8c60ff1ec536700a
Source dataset
uspto-grants-2011_06
Patent number
US07968595B2

Reaction notes

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