1-Hydroxybenzotriazole → 7-methyl-N-[4-(1-methylpropyl)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine-9-carboxamide 2,2-dioxide

HRID 1747847

Reaction equation

HRID 1747847 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:14]([OH:16])=O)[C:5]2[N:10]([CH:11]=1)[CH2:9][CH2:8][S:7](=[O:13])(=[O:12])[N:6]=2.[CH:17]([C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1)([CH2:19][CH3:20])[CH3:18].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.O>[CH3:1][C:2]1[CH:3]=[C:4]([C:14]([NH:25][C:24]2[CH:26]=[CH:27][C:21]([CH:17]([CH3:18])[CH2:19][CH3:20])=[CH:22][CH:23]=2)=[O:16])[C:5]2[N:10]([CH:11]=1)[CH2:9][CH2:8][S:7](=[O:12])(=[O:13])[N:6]=2

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 121771Benzenamine, 4-(1-methylpropyl)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 667489647-Methyl-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine-9-carboxylic acid 2,2-dioxide

Product 1

HCID 668237717-methyl-N-[4-(1-methylpropyl)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine-9-carboxamide 2,2-dioxide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 7-methyl-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine-9-carboxylic acid 2,2-dioxide (76 mg) in DMF (3 mL) were added 4-sec-butylaniline (0.069 mL), HOBt (67 mg), and EDCI HCl (84 mg) and the mixture was stirred at room temperature overnight. To the reaction mixture was added water (10 ml), and the resulting precipitate was collected by filtration. The obtained solid was recrystallized from DMSO-ethanol to give the title compound (114 mg) as pale-yellow crystals.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customThe obtained solid was recrystallized from DMSO-ethanol

Sources & evidence

ORD record
ord-1a59cca17f0e4c9bb80f7efcaa8181ae
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Linked notes

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