5-(2-benzyl-2H-indazol-6-yl)-7-(4-benzylmorpholin-2-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine → HCID 178508828, compound

HRID 1972819Notes

Reaction equation

HRID 1972819 reaction equation
C([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH:27]4[O:32][CH2:31][CH2:30][N:29](CC5C=CC=CC=5)[CH2:28]4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)C1C=CC=CC=1>[Pd].C(O)(=O)C>[N:9]1[NH:8][CH:16]=[C:15]2[C:10]=1[CH:11]=[C:12]([C:17]1[CH:18]=[C:19]([CH:27]3[O:32][CH2:31][CH2:30][NH:29][CH2:28]3)[N:20]3[C:25]=1[C:24]([NH2:26])=[N:23][CH:22]=[N:21]3)[CH:13]=[CH:14]2

Participants

4

Reactant 1

HCID 585293425-(2-benzyl-2H-indazol-6-yl)-7-(4-benzylmorpholin-2-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

Product 1

HCID 178508828HCID 178508828, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 5-(2-benzyl-2H-indazol-6-yl)-7-(4-benzylmorpholin-2-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (200 mg, 0.388 mmol) and 25 mg 10% by wt. palladium on carbon in acetic acid (5 mL) was stirred under an atmosphere of hydrogen for 52 h. The reaction was filtered through Celite® and concentrated in vacuo. The residue was purified by preparative RP-HPLC to provide 35.1 mg (27%) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 8.10 (s, 1 H), 7.92 (s, 1 H), 7.83 (d, 1 H, J=8 Hz), 7.52 (s, 1 H), 7.19 (d, 1 H, J=8 Hz), 6.73 (s, 1 H), 4.98 (dd, 1 H, J=10, 2 Hz) (m, 1 H), 3.81 (d, 1H, J=11 Hz), 3.55-3.66 (m, 2H), 3.31 (bs, 3H), 3.05 (dd, 1H, J=12, 3 Hz), 2.86 (dd, 1H, J=12, 10 Hz), 2.71-2.78 (m, 2H); ES-MS m/z 336.4 [M+H]+, HPLC RT (min) 1.10.

Workup

  1. filtrationThe reaction was filtered through Celite®
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-8629f316880e4a2da2624484d6a6642f
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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