Hydrazine hydrate (1:1) → HCID 57742680, compound

HRID 911848Notes

Reaction equation

HRID 911848 reaction equation
[O:1]([C:8]1[C:9]([NH:21][C:22]2[S:26][N:25]=[C:24]([CH:27]3[CH2:32][CH2:31][N:30]([S:33]([CH2:36][CH2:37][N:38]4C(=O)C5C(=CC=CC=5)C4=O)(=[O:35])=[O:34])[CH2:29][CH2:28]3)[N:23]=2)=[N:10][CH:11]=[C:12]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>CCO>[NH2:38][CH2:37][CH2:36][S:33]([N:30]1[CH2:29][CH2:28][CH:27]([C:24]2[N:23]=[C:22]([NH:21][C:9]3[C:8]([O:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:13][C:12]([S:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=4)=[CH:11][N:10]=3)[S:26][N:25]=2)[CH2:32][CH2:31]1)(=[O:35])=[O:34]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66995152HCID 66995152, compound

Product 1

HCID 57742680HCID 57742680, compoundYield 14.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(2-(4-(5-(3-phenoxy-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-ylsulfonyl)ethyl)isoindoline-1,3-dione (0.110 g, 0.157 mmol) and hydrazine monohydrate (0.0236 g, 0.472 mmol) were dissolved in EtOH (25 mL) and heated to reflux for 8 hours. The reaction was cooled to ambient temperature and the solids filtered and triturated with EtOH to afford the title compound (0.013 g, 14.5% yield). 1H NMR (d6-DMSO) δ 8.38 (d, 1H), 8.36 (m, 1H), 7.66 (dt, 1H), 7.45 (d, 1H), 7.41 (t, 2H), 7.20-7.10 (m, 5H), 3.61 (d, 2H), 3.12 (t, 2H), 3.01-2.89 (m, 5H), 2.09 (d, 2H), 1.79 (m, 2H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 8 hours
  3. filtrationthe solids filtered
  4. customtriturated with EtOH

Sources & evidence

ORD record
ord-a08ba39136914cafb049e0c48ea65a00
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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