1-Hydroxybenzotriazole → N-(4-cyclopropylphenyl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine-9-carboxamide 2,2-dioxide

HRID 1747848Notes

Reaction equation

HRID 1747848 reaction equation
[N:1]1[S:2](=[O:15])(=[O:14])[CH2:3][CH2:4][N:5]2[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([OH:13])=O)[C:6]=12.[CH:16]1([C:19]2[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=2)[CH2:18][CH2:17]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[CH:16]1([C:19]2[CH:25]=[CH:24][C:22]([NH:23][C:11]([C:7]3[C:6]4=[N:1][S:2](=[O:15])(=[O:14])[CH2:3][CH2:4][N:5]4[CH:10]=[CH:9][CH:8]=3)=[O:13])=[CH:21][CH:20]=2)[CH2:18][CH2:17]1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 23846842,2-dioxo-3H,4H-2lambda6-pyrido[2,1-c][1,2,4]thiadiazine-9-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 122539274-Cyclopropylaniline

Product 1

HCID 66748364N-(4-cyclopropylphenyl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine-9-carboxamide 2,2-dioxideYield 74.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3,4-Dihydropyrido[2,1-c][1,2,4]thiadiazine-9-carboxylic acid 2,2-dioxide (150 mg) was dissolved in DMF (5 ml), 4-cyclopropylaniline (131 mg), HOBt (151 mg), EDCI HCl (189 mg) and DIEA (0.23 mL) were added and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was suspended in ethyl acetate, and insoluble crystals were collected by filtration to give the title compound (168 mg) as pale-yellow crystals.

Workup

  1. washwashed successively with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. filtrationinsoluble crystals were collected by filtration

Sources & evidence

ORD record
ord-c54efd75104949d986132ab6e829b78d
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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