Dimethylformamide → HCID 21084060, compound

HRID 347918Notes

Reaction equation

HRID 347918 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[CH:11][C:10]3[C:15]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[S:17][C:9]2=3)=[CH:4][CH:3]=1.[C:29](=[O:32])([O-])[O-].[Cs+].[Cs+].Cl.ClCC[CH:39]1O[CH2:43][CH2:42][NH:41][CH2:40]1.[CH3:45]N(C=O)C>>[O:32]1[CH2:29][CH2:45][N:41]([CH2:40][CH2:39][O:1][C:2]2[CH:3]=[CH:4][C:5]([N:8]3[C:13](=[O:14])[CH:12]=[CH:11][C:10]4[C:15]([C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=5)=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[S:17][C:9]3=4)=[CH:6][CH:7]=2)[CH2:42][CH2:43]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 21084070HCID 21084070, compoundHCID 21914305HCID 21914305, compound

Product 1

HCID 21084060HCID 21084060, compound

Procedure

To a mixture of the compound of Example 89 (100 mg, 0.256 mmol) and caesium carbonate (202 mg, 0.62 mmol) in dry DMF (5 mL) was added 2-(chloroethyl)morpholine hydrochloride (58 mg, 0.31 mmol) and the reaction heated at 60° under nitrogen for 48 h. The reaction was partitioned between water and EtOAc, the EtOAc extracts dried (MgSO4) and concentrated in vacuo. The crude product was then purified by column chromatography on silica eluting with 0–5% MeOH in DCM to give the title compound as a white solid (68 mg). δH (CDCl3) 7.44–7.20 (8H, m), 7.04 (2H, d, J 9 Hz), 6.51 (1H, d, J 10 Hz), 4.15–4.03 (4H, m), 3.68 (4H, m), 2.79 (2H, t, J 6 Hz), 2.54 (4H, m), 1.05 (3H, t, J 7 Hz). LCMS (ES+) RT 2.53 minutes, 505 (M+H)+.

Workup

  1. temperaturethe reaction heated at 60° under nitrogen for 48 h
  2. customThe reaction was partitioned between water and EtOAc
  3. dry with materialthe EtOAc extracts dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was then purified by column chromatography on silica eluting with 0–5% MeOH in DCM

Sources & evidence

ORD record
ord-99b53c39c2e3425da26e4b93a0d98f9e
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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