Hydrazine hydrate (1:1) → HCID 58190592, compound

HRID 1892383Notes

Reaction equation

HRID 1892383 reaction equation
[OH:1][CH2:2][CH:3]([O:6][N:7]1C(=O)C2[C:9](=CC=CC=2)[C:8]1=O)[CH2:4][OH:5].O.NN.[N:21]1[C:30]2[C:25](=[CH:26][C:27]([CH2:31][C:32]3[N:36]4[N:37]=[C:38](C(=O)C)[CH:39]=[CH:40][C:35]4=[N:34][N:33]=3)=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1>>[OH:1][CH2:2][CH:3]([O:6]/[N:7]=[C:8](/[C:35]1[CH:40]=[CH:39][C:38]2[N:33]([C:32]([CH2:31][C:27]3[CH:26]=[C:25]4[C:30](=[CH:29][CH:28]=3)[N:21]=[CH:22][CH:23]=[CH:24]4)=[N:36][N:37]=2)[N:34]=1)\[CH3:9])[CH2:4][OH:5]

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 581904611-(3-(Quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanoneHCID 58190488HCID 58190488, compound2×

Product 1

HCID 58190592HCID 58190592, compoundYield 28.6%

Procedure

The title compound (12 mg, 28.6%) was synthesized from 2-(1,3-dihydroxypropan-2-yloxy)isoindoline-1,3-dione (intermediate B) (152 mg, 0.643 mmol, isomer mixture), hydrazine monohydrate (14 mg, 0.27 mmol) and 1-(3-(quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (41.2) (30 mg, 0.11 mmol) using the same procedure as described in the synthesis of example 44. After purification by HPLC (acidic with 0.05% TFA, then neutralized to basic), the title compound was obtained as a white solid. 1H-NMR (400 MHz, CDCl3) δ ppm 8.89 (d, 1H), 8.12 (d, 1H), 8.08 (d, 1H), 7.97 (d, 1H), 7.86 (s, 1H), 7.82 (d, 1H), 7.73 (d, 1H), 7.42 (m, 1H), 4.77 (s, 2H), 4.49 (m, 1H), 4.00 (dd, 4H), 2.33 (s, 3H). LC-MS (method B): [MH]+=393.2, tR=1.708 min.

Workup

  1. customas described in the synthesis of example 44
  2. customAfter purification by HPLC (acidic with 0.05% TFA
  3. customwas obtained as a white solid

Sources & evidence

ORD record
ord-c01bddbda5064322ab52f4a56ae1421f
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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