Toluene → HCID 178489274, compound

HRID 1262406Notes

Reaction equation

HRID 1262406 reaction equation
[N:1]([Si](C)(C)C)=[N+:2]=[N-:3].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[N:24]2[C:19]([CH:20]=[N:21][C:22]([C:25]#[N:26])=[N:23]2)=[CH:18][CH:17]=1.C1(C)C=CC=CC=1.C([Sn](CCCC)=O)CCC>>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[N:24]2[C:19]([CH:20]=[N:21][C:22]([C:25]3[NH:26][N:3]=[N:2][N:1]=3)=[N:23]2)=[CH:18][CH:17]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 667124197-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine-2-carbonitrile

Product 1

HCID 178489274HCID 178489274, compound

Conditions

Temperature
90 °C

Procedure

Azidotrimethylsilane (0.250 mL, 1.88 mmol) was added to 7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine-2-carbonitrile (48.0 mg, 0.192 mmol) in Toluene (4.0 mL, 38 mmol) and Dibutyloxostannane (50.0 mg, 0.201 mmol) and heat at 90° C. for 4 h. Cool and conc. in vacuo, then purify by prep HPLC. The lyophilate was dissolved in MeOH, loaded onto a Phenomenex sulfonic acid resin, which was washed with MeOH and then the product eluted as the free base with 2M NH3 in MeOH. Conc. and reconc. from DCM afforded 7-(2-Methoxy-phenyl)-2-(1H-tetrazol-5-yl)-pyrrolo[2,1-f][1,2,4]triazine as a yellow film. LCMS (HPLC): 294 (M+H); 1H-NMR (DMSO-d6): 9.25 (s, 1H), 7.83 (m, 1H), 7.47 (m, 1H), 7.23 (m, 2H), 7.11 (m, 3H), 3.83 (s, 3H).

Workup

  1. temperatureCool and conc. in vacuo
  2. custompurify by prep HPLC
  3. dissolutionThe lyophilate was dissolved in MeOH
  4. washwas washed with MeOH
  5. washthe product eluted as the free base with 2M NH3 in MeOH

Sources & evidence

ORD record
ord-e6b4f23db1bd4bd8b9348aa3b7d30b0a
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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