Dimethylformamide → HCID 53235090, compound

HRID 239704Notes

Reaction equation

HRID 239704 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]([C:14]3[O:15][C:16]4[C:21]([C:22](=[O:31])[C:23]=3[C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=3)=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH3:13])[N:9]=[C:10](I)[C:3]=12.C(=O)([O-])[O-].[Na+].[Na+].ClCCl.[CH3:41][N:42]([CH:44]=O)C>C(O)C.O>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]([C:14]3[O:15][C:16]4[C:21]([C:22](=[O:31])[C:23]=3[C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=3)=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH3:13])[N:9]=[C:10]([C:21]3[CH:20]=[C:44]4[C:14]([C:12]([CH3:13])=[N:8][N:42]4[CH3:41])=[CH:23][CH:22]=3)[C:3]=12

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 665799322-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one

Product 1

HCID 53235090HCID 53235090, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of Example 57c (0.400 g, 0.758 mmoles) in DMF (4 ml), ethanol (2 ml) and water (2 ml), intermediate 115 (0.309 g, 1.137 mmoles) and sodium carbonate (0.241 g, 2.27 mmoles) were added and the system is degassed for 30 min. Tetrakistriphenylphosphine Palladium (0.043 g, 0.037 mmoles) was added under nitrogen atmosphere and heated to 80° C. After 12 h, the reaction mixture was celite filtered, concentrated and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with methanol: dichloromethane to afford the title compound as off-white solid (0.071 g, 17% yield). MP: 270-272° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 8.08(s,1H), 8.04(d, J=6.8 Hz, 1H), 7.84(m,2H), 7.69(s,1H), 7.69(d, J=10.8 Hz, 1H), 7.53(t, J=7.5 Hz, 1H), 7.33(d, J=8.3 Hz, 2H), 7.03-6.95(m, 3H), 6.06(q, J=7.1 Hz, 1H), 3.99(s,3H), 2.48(s,3H), 1.92(d, J=7.0 Hz, 3H). Mass: 546.24(M++1).

Workup

  1. customthe system is degassed for 30 min
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography with methanol

Sources & evidence

ORD record
ord-b2c3ae92933b4b6a93bc1ea2fdcd5b1f
Source dataset
uspto-grants-2014_02
Patent number
US08642607B2

Reaction notes

Loading…