Methanol → HCID 11691039, compound

HRID 2249507Notes

Reaction equation

HRID 2249507 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[N:13][C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][CH:16]=2)[CH2:11][CH:10]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:27])=[O:26])[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.O1CCCC1.CO>C1COCC1>[CH2:1]([N:8]1[C:17]2[C:12](=[N:13][C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][CH:16]=2)[CH2:11][CH:10]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:27])=[O:26])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 11540038HCID 11540038, compound

Product 1

HCID 11691039HCID 11691039, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2C (45 mg, 0.096 mmol) in THF (1 mL) at RT under argon was added borane-tetrahydrofuran complex (1 M solution in THF, 0.48 mL, 0.48 mmol) dropwise. After the addition, the reaction became a clear solution. The reaction was allowed to stir at RT under argon for 1 h. After this time, no starting material was detected by LC-MS. MeOH (1 mL) was added carefully to the reaction and the mixture was stirred at RT for 60 min, then concentrated under reduced pressure. The resulting residue was partitioned between CH2Cl2 (30 mL) and saturated aqueous NaHCO3. The layers were separated. The aqueous layer was extracted with CH2Cl2 (20 mL). The combined organic layer were washed with saturated NaCl, dried over Na2SO4, filtered and concentrated. The resultant residue was dissolved in boiling CH3CN (2 μL) and EtOAc (2 mL), and then hexane (10 mL) was added. After cooling to RT. White precipitates foamed. The product was collected by filtration and washed with hexane to give the title compound as a white solid (33 mg, 76%). HPLC (method B): 99% at 5.62 min. MS (ES): m/z 456 [M+H]+. 1H NMR (DMSO6, 400 MHz): δ 8.13 (d, J=6.2 Hz, 1H), 7.92-7.96 (m, 4H), 7.64-7.76 (m, 3H), 7.59 (d, J=8.6 Hz, 1H), 7.29-7.46 (m, 4H), 7.28-7.34 (m, 4H), 7.00 (d, J=8.6 Hz, 1H), 4.54 (dd, J1=48.9 Hz, J2=16.5 Hz, 2H), 3.40-3.45 (m, 1H), 3.36-3.40(m, 1H), 3.25-3.29 (m, 1H), 2.90-3.01(m, 2H).

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred at RT for 60 min
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was partitioned between CH2Cl2 (30 mL) and saturated aqueous NaHCO3
  5. customThe layers were separated
  6. extractionThe aqueous layer was extracted with CH2Cl2 (20 mL)
  7. washThe combined organic layer were washed with saturated NaCl
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. dissolutionThe resultant residue was dissolved
  12. additionhexane (10 mL) was added
  13. temperatureAfter cooling to RT
  14. customWhite precipitates
  15. filtrationThe product was collected by filtration
  16. washwashed with hexane

Sources & evidence

ORD record
ord-f5dca83992b84c728c1cd75e0a276b04
Source dataset
uspto-grants-2008_01
Patent number
US07314882B2

Reaction notes

Loading…