Acetic Acid → HCID 58529960, compound

HRID 1972893Notes

Reaction equation

HRID 1972893 reaction equation
[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH2:27][C:28]4[CH:37]=[C:36]5[C:31]([CH2:32][CH2:33][NH:34][CH2:35]5)=[CH:30][CH:29]=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)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[C:41]1(O[Si](C)(C)C)[CH2:43][CH2:42]1)C.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH2:27][C:28]4[CH:37]=[C:36]5[C:31]([CH2:32][CH2:33][N:34]([CH:41]6[CH2:43][CH2:42]6)[CH2:35]5)=[CH:30][CH:29]=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)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 58529408HCID 58529408, compound

Product 1

HCID 58529960HCID 58529960, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(2-Benzyl-2H-indazol-6-yl)-7-(1,2,3,4-tetrahydro-isoquinolin-7-ylmethyl)-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine (0.100 g, 0.21 mmol) was dissolved in MeOH (1 mL) and (1-ethoxy-cyclopropoxy)-trimethyl-silane (0.22 g, 1.24 mmol) was added followed by acetic acid (0.118 mL, 2.05 mmol) and sodium cyanoborohydride (0.058 g, 0.92 mmol). The resulting mixture was refluxed overnight and then allowed to cool. The mixture was filtered, concentrated and the residue was purified by preparative HPLC to give 55 mg (50%) of the title compound. 1H-NMR (CD3OD-d4) 8.36-8.23 (m, 1 H), 7.81 (s, 1 H), 7.78 (dd, 1H), 7.38-7.29 (m, 4 H), 7.19 (dd, 1 H), 7.10-6.99 (m, 2 H), 6.44 (s, 1 H), 5.63 (s, 2 H), 4.23 (s, 2 H), 3.72 (s, 2 H), 2.96-2.81 (m, 4 H), 1.86-1.79 (m, 1 H), 0.57-0.75 (m, 4 H); LC-MS [M+H]+=426.3, RT=2.32 min.

Workup

  1. temperatureThe resulting mixture was refluxed overnight
  2. temperatureto cool
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-e7b28cacfd1749548819282a7c8f28e0
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

Loading…