Hydrazine hydrate (1:1) → HCID 58190489, compound

HRID 1959699Notes

Reaction equation

HRID 1959699 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[C:16]4=[N:17][C:18](/[C:21](=[N:23]/[O:24][CH2:25][CH2:26][N:27]5C(=O)C6C(=CC=CC=6)C5=O)/[CH3:22])=[CH:19][N:20]=[C:15]4[N:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.O.NN>CO>[NH2:27][CH2:26][CH2:25][O:24]/[N:23]=[C:21](/[C:18]1[N:17]=[C:16]2[N:12]([CH2:11][C:7]3[CH:6]=[C:5]4[C:10](=[CH:9][CH:8]=3)[N:1]=[CH:2][CH:3]=[CH:4]4)[N:13]=[N:14][C:15]2=[N:20][CH:19]=1)\[CH3:22]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58190566HCID 58190566, compound

Product 1

HCID 58190489HCID 58190489, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (E)-2-(2-(1-(1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethylideneaminooxy)ethyl)isoindoline-1,3-dione (70 mg, 0.142 mmol) in MeOH (10 mL) was added hydrazine monohydrate (35.6 mg, 0.711 mmol). The solution was heated at reflux for 30 h and concentrated in vacuo. The crude was purified by column chromatography to afford 19 mg (37%) of the title compound. 1H-NMR (400 MHz, DMSO-d6+D2O) δ ppm 9.35 (s, 1H), 8.98 (s, 1H), 8.35 (d, 1H), 8.02 (s, 1H), 8.01 (d, 1H), 7.81 (d, 1H), 7.53 (m, 1H), 6.20 (s, 2H), 4.47 (s, 2H), 3.22 (s, 2H), 2.34 (s, 3H). LCMS (method B): [MH]+=363, tR=1.57 min.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 30 h
  3. concentrationconcentrated in vacuo
  4. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-233d3c05b92944198f370a3a5eb31550
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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