Ammonia → HCID 58190541, compound

HRID 1892359Notes

Reaction equation

HRID 1892359 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-1a45735ab0844673aea7fa38e77e44a2
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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