Acetyl chloride → HCID 5329910, compound

HRID 1247448Notes

Reaction equation

HRID 1247448 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=3)=[O:20])=[CH:14][CH:13]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2.[C:29](Cl)(=[O:31])[CH3:30]>C1COCC1>[CH3:28][C:24]1[CH:23]=[C:22]([NH:21][C:19]([NH:18][C:15]2[CH:14]=[CH:13][C:12]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:29](=[O:31])[CH3:30])=[C:10]4[C:6]=3[CH2:7][NH:8][C:9]4=[O:11])=[CH:17][CH:16]=2)=[O:20])[CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 5329909HCID 5329909, compound

Product 1

HCID 5329910HCID 5329910, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of Example 3 (0.088 g, 0.24 mmol) in THF (2 mL) was treated dropwise via syringe with acetyl chloride (0.017 mL, 0.24 mmol), stirred at room temperature overnight, quenched with water, cooled to 0° C., and filtered. The filter cake was dried to give 77 mg of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 2.17 (s, 3H); 2.28 (s, 3H); 4.55 (s, 2H); 6.80 (d, J=7.1 Hz, 1H); 7.16 (t, J=7.8 Hz, 1H); 7.24 (d, J=8.1 Hz, 1H); 7.31 (br s, 1H); 7.50 (d, J=8.8 Hz, 2H); 7.56 (d, J=8.8 Hz, 2H); 7.61 (d, J=8.5 Hz, 1H); 8.38 (d, J=8.1 Hz, 1H); 8.62 (s, 1H); 8.78 (s, 1H); 8.96 (s, 1H); 10.58 (s, 1H); MS (ESI(+)) m/e 415 (M+H)+.

Workup

  1. customquenched with water
  2. temperaturecooled to 0° C.
  3. filtrationfiltered
  4. customThe filter cake was dried

Sources & evidence

ORD record
ord-e2fde09ae9e347b0983476843b8d4e2e
Source dataset
uspto-grants-2006_10
Patent number
US07129260B2

Reaction notes

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