Triphenylphosphine → 3-tert-butyl-1-(3-(2-(tetrahydro-2H-pyran-2-yloxy)ethoxy)phenyl)-1H-pyrazol-5-amine

HRID 1402160Notes

Reaction equation

HRID 1402160 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[NH2:15][C:16]1[N:20]([C:21]2[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=2)[N:19]=[C:18]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:17]=1.[O:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH:33]1[O:38][CH2:39][CH2:40]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[C:28]([C:18]1[CH:17]=[C:16]([NH2:15])[N:20]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:40][CH2:39][O:38][CH:33]3[CH2:34][CH2:35][CH2:36][CH2:37][O:32]3)[CH:22]=2)[N:19]=1)([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 41668332-(Oxan-2-yloxy)ethan-1-olHCID 5363146Diisopropyl azodicarboxylateHCID 595579663-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)phenol

Product 1

HCID 579256593-tert-butyl-1-(3-(2-(tetrahydro-2H-pyran-2-yloxy)ethoxy)phenyl)-1H-pyrazol-5-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIAD (847 μL, 4.32 mmol) was added slowly to a solution of 3-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)phenol (US 2006/35922, which is incorporated herein by reference in its entirety; 500 mg, 2.16 mmol), 2-(tetrahydro-pyran-2-yloxy)-ethanol (439 μL, 3.25 mmol) and Ph3P (1.13 g, 4.32 mmol) in THF (10.0 mL) and the mixture stirred for 72 h. The reaction mixture was partitioned between EtOAc (75 mL) and H2O (75 mL) and the aqueous layer extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), filtered and evaporated in vacuo. Purification by FCC, using 5-60% EtOAc in cyclohexane, gave the title compound (1.26 g). LCMS (Method 4): Rt 2.77, m/z 360 [MH+].

Workup

  1. customThe reaction mixture was partitioned between EtOAc (75 mL) and H2O (75 mL)
  2. extractionthe aqueous layer extracted with EtOAc (3×)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification by FCC

Sources & evidence

ORD record
ord-cc16255211d14d548ed1e28d12368cef
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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