Water → HCID 67426946, compound

HRID 2235461Notes

Reaction equation

HRID 2235461 reaction equation
[NH2:1][C:2]1[NH:17][C:5]2=[CH:6][C:7]3[C:8]([CH3:16])([CH3:15])[C:9](=[O:14])[N:10]([CH3:13])[C:11]=3[CH:12]=[C:4]2[N:3]=1.CCN(C(C)C)C(C)C.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>O1CCOCC1>[CH3:13][N:10]1[C:11]2[CH:12]=[C:4]3[N:3]=[C:2]([NH:1][C:27](=[O:34])[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[NH:17][C:5]3=[CH:6][C:7]=2[C:8]([CH3:15])([CH3:16])[C:9]1=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 59300936HCID 59300936, compound

Product 1

HCID 67426946HCID 67426946, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of D1 (210 mg) and DIPEA (4 ml; 23 mmol) in 1,4-dioxane (5.5 ml) is added benzoyl chloride (158 μl) at RT. The mixture is stirred for 20 h at RT and 2 h at 80° C. After completion of the reaction water is added and the aqueous layer is extracted with EtOAc. The combined organic layer is washed with saturated NaHCO3 solution and brine, dried over MgSO4 and concentrated in vacuo. Purification by flash chromatography on silica gel eluting with CH2Cl2/MeOH (98:2) afforded the desired compound (135 mg).

Workup

  1. additionis added
  2. extractionthe aqueous layer is extracted with EtOAc
  3. washThe combined organic layer is washed with saturated NaHCO3 solution and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel eluting with CH2Cl2/MeOH (98:2)

Sources & evidence

ORD record
ord-4cbc69f3b38e4d51a3b42b8dddb3f27c
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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