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

HRID 1405646ノート

反応式

HRID 1405646 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8fa313453a1146cfaae6c71111ad3c57
出典データセット
uspto-grants-2014_12
特許番号
US08916551B2

反応ノート

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