Imidazole → HCID 123162341, compound

HRID 60677Notes

Reaction equation

HRID 60677 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:8]([CH2:21][OH:22])=[N:9][N:10]([CH2:12][CH2:13][O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][O:16]3)[CH:11]=2)[N:5]=[C:4]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:3]=1.N1C=CN=C1.Cl[Si:33]([CH:40]([CH3:42])[CH3:41])([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])[CH3:35]>CN(C=O)C>[C:23]([C:4]1[CH:3]=[C:2]([NH2:1])[N:6]([C:7]2[C:8]([CH2:21][O:22][Si:33]([CH:40]([CH3:42])[CH3:41])([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])[CH3:35])=[N:9][N:10]([CH2:12][CH2:13][O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][O:16]3)[CH:11]=2)[N:5]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 117729489{5-Amino-3-tert-butyl-1'-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1'H-[1,4']bipyrazolyl-3'-yl}-methanol

Product 1

HCID 123162341HCID 123162341, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Intermediate 74e (0.39 g, 1.10 mmol) in DMF (3.9 mL) was treated with imidazole (0.18 g, 2.7 mmol) then chlorotriisopropylsilane (0.28 mL, 1.3 mmol) and the mixture was stirred at RT for 22 h. The mixture was evaporated in vacuo and the residue was partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (2×). The combined organic layers were washed with saturated aqueous sodium bicarbonate solution and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by FCC, using 0-4% MeOH in DCM, to give the title compound (0.44 g, 79%). LCMS (Method 3): Rt 4.20 min, m/z 520 [MH+].

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue was partitioned between EtOAc and water
  3. extractionThe aqueous layer was then extracted with EtOAc (2×)
  4. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate solution and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-130bbb182ef54dd899e73e040ade4864
Source dataset
uspto-grants-2016_09
Patent number
US09440974B2

Reaction notes

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