Acetic Anhydride → HCID 68194652, compound

HRID 2370646Notes

Reaction equation

HRID 2370646 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:14](=[O:15])[C:13]2[CH:16]=[N:17][C:18]([NH:20][C:21]3[CH:30]=[C:29]4[C:24]([C:25]5([CH2:32][CH2:31]5)[CH2:26][NH:27][CH2:28]4)=[CH:23][CH:22]=3)=[N:19][C:12]=2[N:11]2[CH:33]=[CH:34][N:35]=[C:10]12.C(N(C(C)C)CC)(C)C.[C:45](OC(=O)C)(=[O:47])[CH3:46]>CN(C)C=O.C(OCC)(=O)C>[C:45]([N:27]1[CH2:26][C:25]2([CH2:31][CH2:32]2)[C:24]2[C:29](=[CH:30][C:21]([NH:20][C:18]3[N:17]=[CH:16][C:13]4[C:14](=[O:15])[N:9]([C:3]5[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=5[Cl:8])[C:10]5[N:11]([CH:33]=[CH:34][N:35]=5)[C:12]=4[N:19]=3)=[CH:22][CH:23]=2)[CH2:28]1)(=[O:47])[CH3:46]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 68195150HCID 68195150, compound

Product 1

HCID 68194652HCID 68194652, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 109B (200 mg, 0.397 mmol) in 5 mL N,N-dimethylformamide was added diisopropylethylamine (0.346 ml, 1.983 mmol) followed by acetic anhydride (0.041 ml, 0.436 mmol). The reaction mixture was stirred at room temperature overnight, then diluted with ethyl acetate. The organics were washed with saturated aqueous NaHCO3, water, and brine, dried over MgSO4, filtered, and concentrated. The crude material was purified by chromatography was performed with an Analogix 280 with an SF 25-40 column, 0% to 4% methanol/dichloromethane gradient over 30 minutes to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 1.02 (d, J=8.14 Hz, 4H) 2.10 (d, J=21.70 Hz, 3H) 3.46-3.64 (m, 2H) 4.75 (s, 2H) 6.75-7.04 (m, 1H) 7.12 (s, 1H) 7.44-7.90 (m, 6H) 9.16 (s, 1H) 10.80 (s, 1H). MS (ESI+) m/z 546.2 (M+H)+.

Workup

  1. washThe organics were washed with saturated aqueous NaHCO3, water, and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by chromatography
  6. waitwas performed with an Analogix 280 with an SF 25-40 column, 0% to 4% methanol/dichloromethane gradient over 30 minutes

Sources & evidence

ORD record
ord-fa0a370d04ce4a2c9ab9229173de57f2
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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