Sodium triacetoxyborohydride → HCID 54755919, compound

HRID 2089132Notes

Reaction equation

HRID 2089132 reaction equation
[NH:1]1[CH2:4][CH:3]([NH:5][C:6](=[O:22])[CH2:7][NH:8][C:9]2[C:13]3[CH:14]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:16]=[CH:17][C:12]=3[O:11][N:10]=2)[CH2:2]1.[O:23]1[C:27]2[CH:28]=[CH:29][C:30]([CH:32]3[CH2:37][CH2:36][C:35](=O)[CH2:34][CH2:33]3)=[CH:31][C:26]=2[O:25][CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(Cl)Cl.CC(O)C>C(Cl)Cl>[O:23]1[C:27]2[CH:28]=[CH:29][C:30]([CH:32]3[CH2:37][CH2:36][CH:35]([N:1]4[CH2:4][CH:3]([NH:5][C:6](=[O:22])[CH2:7][NH:8][C:9]5[C:13]6[CH:14]=[C:15]([C:18]([F:20])([F:19])[F:21])[CH:16]=[CH:17][C:12]=6[O:11][N:10]=5)[CH2:2]4)[CH2:34][CH2:33]3)=[CH:31][C:26]=2[O:25][CH2:24]1

Participants

6

Reactant 4

HCID 5049666Sodium triacetoxyborohydrideHCID 10932904AGN-PC-0ND25RHCID 21966342Isopropanol methylene chlorideHCID 58548680N-azetidin-3-yl-2-(5-trifluoromethyl-benzo[d]isoxazol-3-ylamino)-acetamide

Product 1

HCID 54755919HCID 54755919, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-azetidin-3-yl-2-(5-trifluoromethyl-benzo[d]isoxazol-3-ylamino)-acetamide (100 mg, 0.318 mmol) and 4-benzo[1,3]dioxol-5-yl-cyclohexanone (69 mg, 0.318 mmol) in DCM (10 mL) was added TEA (55 μL, 0.382 mmol) and the resulting solution was stirred at RT for 30 minutes. Sodium triacetoxyborohydride (81 mg, 0.382 mmol) was then added and the reaction was and stirred at RT overnight. The reaction was dissolved into DCM/IPA (3:1) solution and washed with saturated NaHCO3. The organic layers were dried over anhydrous Na2SO4, concentrated in vacuo and purified by column chromatography using EtOAc (A) and 7N NH3 in MeOH (B) (from 100% A to 10% B in A) to give the above products as white solids. The less polar isomer from the silica gel column was tested in vitro as described in Example 107.

Workup

  1. stirringstirred at RT overnight
  2. washwashed with saturated NaHCO3
  3. dry with materialThe organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-4d04a947182748b18af69a86ace7986d
Source dataset
uspto-grants-2013_05
Patent number
US08436023B2

Reaction notes

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