2-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-Indazole → HCID 58529603, compound

HRID 1972915Notes

Reaction equation

HRID 1972915 reaction equation
C(N1C=C2C(C=C(B3OC(C)(C)C(C)(C)O3)C=C2)=N1)C1C=CC=CC=1.Cl.[CH2:27]([N:34]1[C:42]([CH3:43])=[C:41]2[C:36]([CH:37]=[C:38]([C:44]3[CH:45]=[C:46]([CH:54]4[CH2:59][CH2:58][CH2:57][NH:56][CH2:55]4)[N:47]4[C:52]=3[C:51]([NH2:53])=[N:50][CH:49]=[N:48]4)[CH:39]=[CH:40]2)=[N:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)(Cl)Cl.C(O)(C)C>[CH2:27]([N:34]1[C:42]([CH3:43])=[C:41]2[C:36]([CH:37]=[C:38]([C:44]3[CH:45]=[C:46]([CH:54]4[CH2:59][CH2:58][CH2:57][NH:56][CH2:55]4)[N:47]4[C:52]=3[C:51]([NH2:53])=[N:50][CH:49]=[N:48]4)[CH:39]=[CH:40]2)=[N:35]1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 585293132-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-IndazoleHCID 69304221HCID 69304221, compound

Product 1

HCID 58529603HCID 58529603, compound

Reagents, catalysts & solvents 1

HCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

Using the procedures described in Steps 1-6 of Intermediate SS and substituting 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-ol-2-benzyl-3-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole (1:1) for Intermediate C, 5-(2-benzyl-3-methyl-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 7.89 (s, 1 H), 7.76 (d, 1 H), 7.53 (s, 1 H), 7.24-7.38 (m, 3 H), 7.21 (d, 2 H), 7.08 (dd, 1 H), 6.58 (s, 1 H), 5.64 (s, 2 H), 3.14-3.30 (m, 3H,) 2.93 (d, 1 H), 2.62 (s, 3 H), 2.50-2.59 (m, 1 H), 2.01-2.11 (m, 1 H), 1.43-1.70 (m, 3 H); ES-MS m/z 438.39 [M+H]+, HPLC RT (min) 2.10.

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-4662c1ca4436477eb5ebdc6dd190666b
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

Loading…