Methyl iodide → HCID 90412921, compound

HRID 2175982Notes

Reaction equation

HRID 2175982 reaction equation
[F:1][C:2]1[C:3]([C:28]2[N:33]=[CH:32][CH:31]=[CH:30][N:29]=2)=[C:4]([C:8]([N:10]2[C@@H:14]3[CH2:15][CH2:16][C@H:11]2[C@H:12]([NH:17][C:18]2[CH:23]=[N:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][N:19]=2)[CH2:13]3)=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH3:34]C(C)([O-])C.[Na+].IC>CN(C=O)C.CCOC(C)=O.O>[F:1][C:2]1[C:3]([C:28]2[N:29]=[CH:30][CH:31]=[CH:32][N:33]=2)=[C:4]([C:8]([N:10]2[C@@H:14]3[CH2:15][CH2:16][C@H:11]2[C@H:12]([N:17]([CH3:34])[C:18]2[CH:23]=[N:22][C:21]([C:24]([F:25])([F:27])[F:26])=[CH:20][N:19]=2)[CH2:13]3)=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 23676156Sodium t-butoxideHCID 90412187HCID 90412187, compound

Product 1

HCID 90412921HCID 90412921, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound of Example 238 (63 mg, 0.14 mmol) was dissolved in DMF (1.4 mL) and then sodium tert-butoxide (15 mg, 0.15 mmol) followed by iodomethane (9 μL, 0.14 mmol) were added. After 15 h at room temperature the reaction mixture was diluted with EtOAc and water was added. The aqueous phase was extracted twice with EtOAc and the combined organic phases were dried over MgSO4, filtered and evaporated. Purification was performed using Agilent prep method X to give the title compound (40 mg, 62%). MS (ESI) mass calcd. for: C23H20F4N6O, 472.2. m/z found 473.2 [M+H]+. 1H NMR (500 MHz, Chloroform-d) 8.81 (d, J=4.9 Hz, 2H), 8.35 (s, 1H), 8.02 (s, 1H), 7.55-7.46 (m, 1H), 7.34-7.20 (m, 3H), 4.81-4.73 (m, 1H), 4.67 (d, J=4.3 Hz, 1H), 4.17-4.08 (m, 1H), 3.05 (s, 3H), 2.12 (dd, J=12.8, 8.3 Hz, 1H), 1.98-1.44 (m, 5H).

Workup

  1. additionwere added
  2. additionwas added
  3. extractionThe aqueous phase was extracted twice with EtOAc
  4. dry with materialthe combined organic phases were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customPurification

Sources & evidence

ORD record
ord-34b39a5df38c448fbb3f8f22aaedf9d3
Source dataset
uspto-grants-2015_06
Patent number
US09062078B2

Reaction notes

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