Triethylamine → HCID 136071815, compound

HRID 2108587Notes

Reaction equation

HRID 2108587 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH:12]([CH3:21])[CH:13](O)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]=1[NH2:11])=[O:5])[CH3:2].O=S(Cl)Cl.CCN(CC)CC>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]2[CH:12]([CH3:21])[CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:11][C:10]=12)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 57631607HCID 57631607, compound

Product 1

HCID 136071815HCID 136071815, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 2 (0.80 g, 2.8 mmol) was dissolved in CH2Cl2. SOCl2 (0.61 mL, 8.3 mmol) was added dropwise. After 90 minutes, the solution was concentrated to give a yellow solid. After pumping on high vacuum for 5 minutes, the solid was dissolved in CHCl3. Et3N (2.7 mL, 19.5 mmol) was added dropwise and the reaction mixture stirred for 1 hour. The reaction was quenched with water and diluted with AcOEt. The solution was washed with sat. NH4Cl, sat. NaHCO3, brine, and then dried (MgSO4). Flash chromatography (20% AcOEt/hexane) gave both the syn (0.10 g, 14%) and anti (0.62 g, 82%) isomers 3. Anti isomer 1H NMR (400 MHz, CDCl3) δ 1.23 (t, J=7.0 Hz, 3H), 1.80 (d, J=6.6 Hz, 3H), 4.10-4.20 (m, 2H), 4.25-4.35 (m, 1H), 4.38 (brs, 1H), 5.10 (d, J=9.8 Hz, 1H), 7.17-7.25 (m, 5H), 7.59 (s, 1H). Syn isomer 1H NMR (400 MHz, CDCl3) δ 1.28 (d, J=7.0 Hz, 3H), 7.38 (t, J=7.4 Hz, 3H), 4.25-4.35 (m, 2H), 7.43-7.52 (m, 1H), 5.17 (brs, 1H), 5.23 (d, J=9.8 Hz, 1H), 7.37-7.45 (m, 5H).

Workup

  1. concentrationthe solution was concentrated
  2. customto give a yellow solid
  3. waitAfter pumping on high vacuum for 5 minutes
  4. customThe reaction was quenched with water
  5. additiondiluted with AcOEt
  6. washThe solution was washed with sat. NH4Cl, sat. NaHCO3, brine
  7. dry with materialdried (MgSO4)
  8. customFlash chromatography (20% AcOEt/hexane) gave both the syn (0.10 g, 14%) and anti (0.62 g, 82%)

Sources & evidence

ORD record
ord-6a0944887bef4866abc35ab4ebc6540b
Source dataset
uspto-grants-2009_04
Patent number
US07514441B2

Reaction notes

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