Chloroacetamide → HCID 44581498, compound

HRID 971156Notes

Reaction equation

HRID 971156 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:29])[N:15]([C:18]4[CH:23]=[CH:22][C:21]([C:24]5([NH:27][CH3:28])[CH2:26][CH2:25]5)=[CH:20][CH:19]=4)[CH2:16][CH2:17][C:12]=3[C:11]([C:30]([F:33])([F:32])[F:31])=[N:10]2)=[CH:5][CH:4]=1.[C:34]([O-])([O-])=O.[K+].[K+].ClC[C:42]([NH2:44])=[O:43].CCOC(C)=O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:29])[N:15]([C:18]4[CH:23]=[CH:22][C:21]([C:24]5([N:27]([CH3:34])[CH2:28][C:42]([NH2:44])=[O:43])[CH2:26][CH2:25]5)=[CH:20][CH:19]=4)[CH2:16][CH2:17][C:12]=3[C:11]([C:30]([F:32])([F:33])[F:31])=[N:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6580ChloroacetamideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 44581495HCID 44581495, compound

Product 1

HCID 44581498HCID 44581498, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

The product of Example 130 (50 mg, 0.11 mmol) was stirred in DMF (0.3 mL). K2CO3 (45 mg, mmol, 0.33 mmol, 3 eq) and chloroacetamide (20 mg, 0.21 mmol, 2 eq) were added. The mixture was stirred at 70° C. for 2 h. EtOAc was added, washed with H2O and brine, dried over MgSO4, filtered, and concentrated. The residue was purified by Silica gel purification to yield the title compound. LC/MS (ESI+) 514.8 (M+H)+, tR=2.00 min (10–90% CH3CN/H2O in a 4-min run). 1H NMR (CDCl3) δ 87.46 (d, J=9.2 Hz, 2H), 7.27 (m, 4H), 6.91 (d, J=8.8 Hz, 2H), 4.12 (t, J=6.6 Hz, 2H), 3.81 (s, 3H), 3.15 (m, 4H), 2.29 (m, 3H), 0.97 (m, 2H), 0.87 (m, 2H) ppm.

Workup

  1. washwashed with H2O and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by Silica gel purification

Sources & evidence

ORD record
ord-f93541b2ecf04cc8bfb4d23bada196a1
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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