Acetic Acid → HCID 68694848, compound

HRID 2245001Notes

Reaction equation

HRID 2245001 reaction equation
[CH3:1][N:2]([N:4]=[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH:13]([NH:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)=[O:23])[C:12]2=[O:32])=[CH:7][CH2:6]1)[CH3:3].N1CC[CH2:35][CH2:34]1.CC(O)=O>>[N:2]1([N:4]=[C:5]2[CH:6]=[CH:7][C:8]([N:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH2:14][CH:13]([NH:21][C:22]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)=[O:23])[C:12]3=[O:32])=[CH:9][CH2:10]2)[CH2:1][CH2:35][CH2:34][CH2:3]1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 68691277HCID 68691277, compound

Product 1

HCID 68694848HCID 68694848, compoundYield 50%

Procedure

To the thioimidate solution in MeOH (4 mL, 0.063 mmol) from Example 134, a pre-mixed pyrrolidine (0.037 mL, 0.44 mmol) and HOAc (0.040 mL, 0.70 mmol) were added. The mixture was heated to reflux for 1 h, then was stirred at room temperature overnight. After being concentrated in vacuo, the residue was purified by HPLC to give a white powder (15 mg). MS 488.3 and 490.3 (M+H, Cl pattern).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 h
  3. concentrationAfter being concentrated in vacuo
  4. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-bbf0e8ac7b1b47fba45731bf0c15b71f
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

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