2-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-Indazole → HCID 58529931, compound

HRID 1972917Notes

Reaction equation

HRID 1972917 reaction equation
C(N1C=C2C(C=C(B3OC(C)(C)C(C)(C)O3)C=C2)=N1)C1C=CC=CC=1.Cl.[C:27]1([N:33]2[CH:41]=[C:40]3[C:35]([CH:36]=[C:37]([C:42]4[CH:43]=[C:44]([CH:52]5[CH2:57][CH2:56][CH2:55][NH:54][CH2:53]5)[N:45]5[C:50]=4[C:49]([NH2:51])=[N:48][CH:47]=[N:46]5)[CH:38]=[CH:39]3)=[N:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)(Cl)Cl.C(O)(C)C>[C:27]1([N:33]2[CH:41]=[C:40]3[C:35]([CH:36]=[C:37]([C:42]4[CH:43]=[C:44]([CH:52]5[CH2:57][CH2:56][CH2:55][NH:54][CH2:53]5)[N:45]5[C:50]=4[C:49]([NH2:51])=[N:48][CH:47]=[N:46]5)[CH:38]=[CH:39]3)=[N:34]2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 585293132-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-IndazoleHCID 69328943HCID 69328943, compound

Product 1

HCID 58529931HCID 58529931, compound

Reagents, catalysts & solvents 1

HCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

Using the procedures described in Steps 1-6 of Intermediate SS and substituting 2-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-Indazole for Intermediate C, 5-(2-phenyl-2H-indazol-6-yl)-7-piperidin-3-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine hydrochloride was prepared. The salt was dissolved in 3:1 CHCl3/isopropanol (25 mL). The mixture was washed with saturated, aqueous NaHCO3 (25 mL), brine, dried (Na2SO4) and concentrated to dryness to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 9.19 (s, 1 H), 8.12 (d, 2 H), 7.80-8.02 (m, 2 H), 7.71 (s, 1 H), 7.54-7.79 (m, 2 H), 7.39-7.54 (m, 1 H), 7.25 (d, 1 H), 6.67 (s, 1 H), 3.19-3.48 (m, 3 H), 2.93-3.05 (m, 1 H), 2.48-2.73 (m, 2 H), 2.01-2.17 (m, 1 H), 1.46-1.82 (m, 2 H); ES-MS m/z 410.36 [M+H]+, HPLC RT (min) 2.05.

Workup

  1. customwas prepared
  2. washThe mixture was washed with saturated, aqueous NaHCO3 (25 mL), brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-cc6db00eea9645539df9f2cf06a0ddcc
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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