Acetic Acid → HCID 58333418, compound

HRID 2066852Notes

Reaction equation

HRID 2066852 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25]([F:27])[C:24]([NH2:28])=[CH:23][C:22]=3[F:29])[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[O-:30][C:31]#[N:32].[K+].C(O)(=O)C>C1COCC1.O>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25]([F:27])[C:24]([NH:28][C:31]([NH2:32])=[O:30])=[CH:23][C:22]=3[F:29])[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 11378442Potassium cyanateHCID 583334444-[1-(4-Amino-2,5-difluoro-phenyl)-piperidin-4-ylideneaminooxy]-piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 58333418HCID 58333418, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 34-1 (72.5 mg, 0.18 mmol) in THF (1 mL) and water (1 mL), was added potassium cyanate (30 mg, 0.37 mmol), acetic acid (0.2 mL) and water (1.8 mL). The biphasic solution was stirred at room temperature for 2 h then concentrated, dissolved in DCM and purified on preparative HPLC to give 37-1: LC-MS 454.1 (MH), tR=6.42 (Method 2). EC50: 71 nM.

Workup

  1. concentrationthen concentrated
  2. dissolutiondissolved in DCM
  3. custompurified on preparative HPLC
  4. customto give 37-1

Sources & evidence

ORD record
ord-6ac43aaaf9124d4c938a78782e823d44
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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