Bromotrichloromethane → HCID 59278415, compound

HRID 559703Notes

Reaction equation

HRID 559703 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][S:8][C:7]([CH:10]([NH:13][C:14]([C:16]2[C:17]3[CH:24]=[N:23][N:22]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)[C:18]=3[CH:19]=[N:20][CH:21]=2)=[O:15])[CH2:11][CH3:12])=[N:6]1)=[O:4].C1CCN2C(=NCCC2)CC1.BrC(Cl)(Cl)Cl>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH:10]([NH:13][C:14]([C:16]2[C:17]3[CH:24]=[N:23][N:22]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)[C:18]=3[CH:19]=[N:20][CH:21]=2)=[O:15])[CH2:11][CH3:12])[S:8][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 6383BromotrichloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59278513HCID 59278513, compound

Product 1

HCID 59278415HCID 59278415, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a chilled (0° C.) solution of (R)-2-(1-{[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-propyl)-4,5-dihydro-thiazole-4-carboxylic acid methyl ester (0.296 g, 0.670 mmol) and DBU (200 μL, 1.34 mmol) in CH2Cl2 (8.0 mL) was added BrCCl3 (69.0 μL, 0.700 mmol). The mixture was then warm to room temperature. After 18 hours, the reaction mixture was diluted with CH2Cl2 (20 mL) and washed with saturated aqueous ammonium chloride (3×10 mL). The organic layer was washed with saturated aqueous sodium bicarbonate (10 mL) and brine (10 mL), dried over MgSO4, filtered and concentrated. The mixture was purified by silica gel chromatography eluting with a gradient of 0-80% ethyl acetate in heptane to afford the title compound. MS m/z 440.77 (MH+).

Workup

  1. washwashed with saturated aqueous ammonium chloride (3×10 mL)
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate (10 mL) and brine (10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe mixture was purified by silica gel chromatography
  7. washeluting with a gradient of 0-80% ethyl acetate in heptane

Sources & evidence

ORD record
ord-3f22da6e0a3e4d35a5c58bc1bca0b596
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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