Isopropanol → HCID 56848821, compound

HRID 1470365Notes

Reaction equation

HRID 1470365 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:24][C:25]([C:27]2[C:28](=[O:41])[N:29]([C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)[CH:30]=[CH:31][C:32]=2I)=[O:26])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:17][C:10]=12.CC(O)C.[CH3:46][NH2:47]>O>[F:1][C:2]1[CH:3]=[C:4]([NH:24][C:25]([C:27]2[C:28](=[O:41])[N:29]([C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)[CH:30]=[CH:31][C:32]=2[NH:47][CH3:46])=[O:26])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:17][C:10]=12

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 6329MethylamineHCID 66779963HCID 66779963, compound

Product 1

HCID 56848821HCID 56848821, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a 2 mL microwave tube with stirbar was added 1-(4-fluoro-phenyl)-4-iodo-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid [3-fluoro-4-(2-phenyl-furo[3,2-b]pyridin-7-yloxy)-phenyl]-amide (45.00 mg; 0.07 mmol; 1.00 eq.) and iPrOH (1.00 ml) and the vial was sealed and flushed with N2. To the reaction mixture was added a solution of methylamine (0.05 ml; 0.54 mmol; 8.00 eq.) 40% in water. The reaction mixture was heated to 100° C. in a microwave reactor for 1 h. The reaction mixture was cooled to room temperature and the white precipitate was filtered, washed methanol, and dried under vacuo to afford the title compound as a white solid (19 mg, 49%). (HPLC (method F): 94%, RT: 4.96 min); 1H NMR (400 MHz, DMSO-d6) δ [ppm] 10.46 (d, J=5.1, 1H), 8.36 (d, J=5.6, 1H), 8.02 (dd, J=13.3, 2.4, 1H), 7.96-7.89 (m, 2H), 7.75 (d, J=7.8, 1H), 7.71 (s, 1H), 7.56-7.44 (m, 6H), 7.42-7.32 (m, 3H), 6.74 (d, J=5.0, 1H), 6.27 (d, J=7.9, 1H), 3.03 (d, J=5.1, 3H); MS (m/z) 565 [M+H]+, RT: 4.3 min.

Workup

  1. customthe vial was sealed
  2. customflushed with N2
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationthe white precipitate was filtered
  5. washwashed methanol
  6. customdried under vacuo

Sources & evidence

ORD record
ord-454403ebd53e4357ad9bf65bf0681512
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

Loading…