Ammonia → HCID 58190541, compound

HRID 1959697Notes

Reaction equation

HRID 1959697 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][C:26]([O:28]C)=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.[NH3:30]>>[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][C:26]([NH2:30])=[O:28])/[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

Participants

3

Reactant 2

HCID 222AmmoniaHCID 58190484HCID 58190484, compound

Product 1

HCID 58190541HCID 58190541, compoundYield 16%

Procedure

To a solution of (E)-methyl 2-(1-(1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethylideneaminooxy)acetate (example 31) (70 mg, 0.179 mmol) was added ammonia (2 N, 0.268 mL, 0.537 mmol). The reaction was heated at reflux for 12 h. The reaction mixture was concentrated in vacuo to give a crude product which was purified by prep-HPLC to afford 9 mg (16%) of the title compound. 1H-NMR (400 MHz, DMSO-d6+D2O) δ ppm 9.32 (s, 1H), 8.88 (d, 1H), 8.34 (d, 1H), 8.01 (m, 2H), 7.81 (d, 1H), 7.52 (dd, 1H), 7.33 (br, 2H), 6.20 (s, 2H), 4.67 (s, 2H), 2.27 (s, 3H). LCMS (method B): [MH]+=377, tR=1.06 min.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 12 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto give a crude product which
  5. customwas purified by prep-HPLC

Sources & evidence

ORD record
ord-2c9aeab895e34937b22c655c7db828e7
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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