3-Tert-butyl-1,2-oxazol-5-amine → HCID 71295250, compound

HRID 868815Notes

Reaction equation

HRID 868815 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([O:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[C:12]([CH:15]=2)[C:13]#[N:14])[CH:5]=[CH:4][N:3]=1.[C:23]([C:27]1[CH:31]=[C:30]([NH2:32])[O:29][N:28]=1)([CH3:26])([CH3:25])[CH3:24].CC([O-])(C)C.[K+]>O1CCOCC1>[C:23]([C:27]1[CH:31]=[C:30]([NH:32][C:2]2[CH:7]=[C:6]([C:8]3[CH:9]=[CH:10][C:11]([O:16][CH:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[C:12]([CH:15]=3)[C:13]#[N:14])[CH:5]=[CH:4][N:3]=2)[O:29][N:28]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 20956943-Tert-butyl-1,2-oxazol-5-amineHCID 23665647Potassium tert-butoxideHCID 71295370HCID 71295370, compound

Product 1

HCID 71295250HCID 71295250, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

100 mg of 5-(2-fluoropyridin-4-yl)-2-(tetrahydropyran-4-yloxy)benzonitrile are suspended in 6 ml of dioxane in a 50 ml three-necked flask under N2, 52 mg of 3-tert-butylisoxazol-5-ylamine and 79 mg of KOtBu are added. The yellow solution is stirred at 80° C. for 2.5 h. For work-up, the reaction mixture is evaporated in a rotary evaporator, the residue is taken up in ethyl acetate and water and extracted. The collected organic phases are dried, filtered and evaporated. The crude product is purified by preparative HPLC, giving the desired product in 46% yield; HPLC-MS Rt. [min] 2.556; HPLC-MS [M+H] 419;

Workup

  1. customFor work-up, the reaction mixture is evaporated in a rotary evaporator
  2. extractionwater and extracted
  3. customThe collected organic phases are dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-acc971eb0ceb44f498a70c234ff3969c
Source dataset
uspto-grants-2015_03
Patent number
US08969335B2

Reaction notes

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