Benzoyl chloride → HCID 59785907, compound

HRID 1673244Notes

Reaction equation

HRID 1673244 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C@@H:25]([OH:26])[CH2:24][C:23]([CH3:28])([CH3:27])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1.CCN(CC)CC.[C:36](Cl)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:36]([O:26][C@@H:25]1[C:10]2[C:11](=[N:12][C:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH:9]=2)[O:22][C:23]([CH3:28])([CH3:27])[CH2:24]1)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 67020012HCID 67020012, compound

Product 1

HCID 59785907HCID 59785907, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Step A (21.6 mg, 0.05 mmol), NEt3 (21 μL, 0.15 mmol), and catalytic amount of DMAP in 10 mL of CH2Cl2 at rt was added benzoyl chloride (11.5 μL, 0.10 mmol). After stirring for 2 h, the reaction was quenched by adding saturated aq NaHCO3 (5 mL) and the resulting mixture was stirred at rt for 30 min. The reaction mixture was partitioned between CH2Cl2 (50 mL) and saturated aq NaHCO3 (50 mL). The aq layer was separated and extracted with CH2Cl2 (3×10 mL). The organic layers were combined, dried over MgSO4, and concentrated. Chromatography on Biotage 40+S cartridges using 3:17 v/v EtOAc/hexanes as the eluant afforded the title compound: 1H NMR δ 1.57 (s, 3H), 1.65 (s, 3H), 2.24 (dd, J=6.7, 14.2, 1H), 2.46 (dd, J=5.9, 14.3, 1H), 6.40 (t, J=6.2, 1H), 7.00 (d, J=8.4, 2H), 7.16-7.28 (m, 5H), 7.45-7.60 (m, 3H), 7.77 (s, 1H), 8.07 (d, J=7.5, 2H).

Workup

  1. customthe reaction was quenched
  2. additionby adding saturated aq NaHCO3 (5 mL)
  3. stirringthe resulting mixture was stirred at rt for 30 min
  4. customThe reaction mixture was partitioned between CH2Cl2 (50 mL) and saturated aq NaHCO3 (50 mL)
  5. customThe aq layer was separated
  6. extractionextracted with CH2Cl2 (3×10 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-44d5ac2879714bc9b7cc07ba1b7543ad
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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