Hydrazine hydrate (1:1) → HCID 21914784, compound

HRID 1246524Notes

Reaction equation

HRID 1246524 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:22]=[C:23]([NH:36][C:37](=[O:39])[CH3:38])[S:24][C:25]=2[C:26]2[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][CH:27]=2)=[CH:17][CH:16]=1.O.NN>C(#N)C>[NH2:3][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[N:22]=[C:23]([NH:36][C:37](=[O:39])[CH3:38])[S:24][C:25]=2[C:26]2[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][CH:27]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21914848HCID 21914848, compound

Product 1

HCID 21914784HCID 21914784, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-{4-(4-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]phenyl}-5-[4-(methylsulfonyl)phenyl]-1,3-thiazol-2-yl)acetamide (53.2 mg) in acetonitrile (0.5 ml) was added hydrazine monohydrate (46.1 μl), and the mixture was stirred at 50° C. for 30 min. The volatiles were evaporated. To the mixture was added chloroform (1 ml), and an insoluble material was removed by filtration. The filtrate was purified by preparative thin-layer chromatography over NH silica gel with chloroform/methanol (10:1) as an eluent to give N-{4-[4-(3-aminopropyl)phenyl]-5-[4-(methylsulfonyl)phenyl]-1,3-thiazol-2-yl}acetamide as a yellow solid.

Workup

  1. customThe volatiles were evaporated
  2. additionTo the mixture was added chloroform (1 ml)
  3. customan insoluble material was removed by filtration
  4. customThe filtrate was purified by preparative thin-layer chromatography over NH silica gel with chloroform/methanol (10:1) as an eluent

Sources & evidence

ORD record
ord-ba7c4b6ab0f64d8d87b5a6c31c5b7ccc
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

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