Acetic Anhydride → HCID 23433979, compound

HRID 2121643Notes

Reaction equation

HRID 2121643 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:12]=[C:11]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:10]2[C:5](=[CH:6][C:7]([NH2:23])=[C:8]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH:9]=2)[N:4]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>C(O)(=O)C>[ClH:1].[CH3:2][C:3]1[CH:12]=[C:11]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:10]2[C:5](=[CH:6][C:7]([NH:23][C:24](=[O:26])[CH3:25])=[C:8]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH:9]=2)[N:4]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 23433938HCID 23433938, compound

Product 1

HCID 23433979HCID 23433979, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution 0.1 g (0.27 mmol of 2-methyl-4,6-di-pyrrolidin-1-yl-quinolin-7-ylamine hydrochloride (×1.58 HCl), product of example 70 in acetic acid (0.22 ml) was treated with 0.1 ml (1.08 mmol) of acetic anhydride and then stirred at RT for 19 h. The reaction mixture was concentrated in vacuo, brought to pH 9 with conc. ammonia and then twice extacted with CH2CL2. The organic phase was washed with water saturated with brine and dried over magnesium sulfate. The solvent was removed in vacuo, the residue triturated with ether (10 ml) and treated tropwise with 0.3 ml of 3 N HCL in MeOH. The brown crystalline solid obtained was filtered off by suction and dried in a high vacuum to give 58.7 mg (89%) of N-(2-methyl-4,6-di-pyrrolidin-1-yl-quinolin-7-yl)-acetamide hydrochloride as a brown solid. ISP mass spectrum, m/e: 339.3 (M+1 calculated for C20H27N4O: 339).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washThe organic phase was washed with water saturated with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. customthe residue triturated with ether (10 ml)
  6. additiontreated tropwise with 0.3 ml of 3 N HCL in MeOH
  7. customThe brown crystalline solid obtained
  8. filtrationwas filtered off by suction
  9. customdried in a high vacuum

Sources & evidence

ORD record
ord-d439a46539894565bc5ee250e945cddb
Source dataset
uspto-grants-2004_02
Patent number
US06696467B2

Reaction notes

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