Acetic Acid → HCID 68694017, compound

HRID 2244974Notes

Reaction equation

HRID 2244974 reaction equation
[CH3:1][N:2]([N:4]=[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:31])[CH:13]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[NH:14][C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[O:16])=[C:7]([F:32])[CH2:6]1)[CH3:3].N1CC[CH2:34]1.CC(O)=O>>[N:2]1([N:4]=[C:5]2[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:31])[CH:13]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[NH:14][C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)=[O:16])=[C:7]([F:32])[CH2:6]2)[CH2:1][CH2:34][CH2:3]1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 10422AzetidineHCID 68689748HCID 68689748, compound

Product 1

HCID 68694017HCID 68694017, compoundYield 18.1%

Procedure

To the thioimidate solution in MeOH (4 mL, 0.284 mmol) from EXAMPLE 33, a pre-mixed azetidine (0.096 mL, 1.43 mmol) and HOAc (0.122 mL, 2.14 mmol) were added. The mixture was then stirred at room temperature overnight. After being concentrated in vacuo, the residue was purified by HPLC to give a white powder (24 mg). MS 480.1 and 482.1 (M+H, Cl pattern).

Workup

  1. concentrationAfter being concentrated in vacuo
  2. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-5b5eab8345144c47b49d31cf1454d61a
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

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