Formamide → HCID 58906455, compound

HRID 1294577Notes

Reaction equation

HRID 1294577 reaction equation
[CH3:1][C:2]1([CH3:28])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH2:5][CH:6]2[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][C:14](NC2C=CC=C(F)C=2)(C(N)=O)[CH2:13][CH2:12]1.[BH4-].[Na+].C(N)=[O:32]>>[CH3:1][C:2]1([CH3:28])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH2:5][CH:6]2[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][C:14](=[O:32])[CH2:13][CH2:12]1

Participants

4

Reactant 3

HCID 713FormamideHCID 4311764Sodium borohydrideHCID 69471805HCID 69471805, compound

Product 1

HCID 58906455HCID 58906455, compound

Procedure

A solution of 29.3 g (76 mmol) of (29a) in 400 ml formamide was heated for 2 h at 200° C. The solution turned from yellow to black. The reaction was monitored by 1H-NMR. After completed reaction the mixture was cooled to room temperature and poured into ice-water (800 g). The mixture was extracted with DCM (6×1 l). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in 1.2 l of methanol and 4.3 g (114 mmol) of sodiumborohydride were added portion wise. The mixture was stirred for 1 h at room temperature and another hour at 60° C. The reaction mixture was cooled to room temperature and quenched with 25 ml of water. The solvent was evaporated in vacuo. The residue was dissolved in 750 ml of ammonia and extracted with DCM (7×1.5 l). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give 24.8 g of crude product, which was purified by column chromatography (SiO2, heptane:EtOAc, 1:1→1:3). Trituration with Et2O of the eluated product yielded 3.44 g (8.6 mmol, 11.3% from compound (26)) of compound (30a) as a white solid.

Workup

  1. customreaction the mixture
  2. extractionThe mixture was extracted with DCM (6×1 l)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in 1.2 l of methanol
  6. temperatureThe reaction mixture was cooled to room temperature
  7. customquenched with 25 ml of water
  8. customThe solvent was evaporated in vacuo
  9. dissolutionThe residue was dissolved in 750 ml of ammonia
  10. extractionextracted with DCM (7×1.5 l)
  11. dry with materialThe combined organic layers were dried over Na2SO4
  12. concentrationconcentrated in vacuo
  13. customto give 24.8 g of crude product, which
  14. customwas purified by column chromatography (SiO2, heptane:EtOAc, 1:1→1:3)

Sources & evidence

ORD record
ord-480fcb6f1df142c299ebd4ef747c7a3c
Source dataset
uspto-grants-2007_07
Patent number
US07241770B2

Reaction notes

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