Isopropanol → 4-[(3-Chloro-4-methoxybenzyl)amino]-1(4-hydroxypiperidino)-6-phthalazine carbothiamide

HRID 47346

Reaction equation

HRID 47346 reaction equation
P([O-])(OCC)(SCC)=[S:2].[Cl:10][C:11]1[CH:12]=[C:13]([CH:35]=[CH:36][C:37]=1[O:38][CH3:39])[CH2:14][NH:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:26]#[N:27])[CH:24]=2)[C:19]([N:28]2[CH2:33]CCC[CH:29]2O)=[N:18][N:17]=1.[CH:40]([OH:43])([CH3:42])[CH3:41]>O>[Cl:10][C:11]1[CH:12]=[C:13]([CH:35]=[CH:36][C:37]=1[O:38][CH3:39])[CH2:14][NH:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:26](=[S:2])[NH2:27])[CH:24]=2)[C:19]([N:28]2[CH2:33][CH2:42][CH:40]([OH:43])[CH2:41][CH2:29]2)=[N:18][N:17]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 53249491DiethyldithiophosphateHCID 865883124-[(3-Chloro-4-methoxybenzyl)amino]-1-(hydroxypiperidino)-6-phthalazine carbonitrile

Product 1

HCID 99338344-[(3-Chloro-4-methoxybenzyl)amino]-1(4-hydroxypiperidino)-6-phthalazine carbothiamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3.7 ml diethyl dithiophosphate was added to a mixture of 2.0 g 4-[(3-chloro-4-methoxybenzyl)amino]-1-(hydroxypiperidino)-6-phthalazine carbonitrile, 1 ml water and 2 ml isopropanol, and the mixture was heated under reflux for 1 hr. After cooling, water was added to the reaction solution and the resulting crystals were collected by filtration. The filtrate was extracted with ethyl acetate and washed with brine. It was dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated, and the resulting crystalline residue was combined with the crystals collected above by filtration, whereby 1.5 g of the title compound was obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. temperatureAfter cooling
  4. filtrationthe resulting crystals were collected by filtration
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialIt was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customThe filtrate was evaporated
  10. filtrationcollected above by filtration

Sources & evidence

ORD record
ord-5695479b783148a5bdc14f2c5cdf229d
Source dataset
uspto-grants-2004_03
Patent number
US06699870B2

Linked notes

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