1,2-Dichloroethane → N-(2-Aminophenyl)-1-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)azetidine-3-carboxamide

HRID 2202826ノート

反応式

HRID 2202826 の反応式
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([N:15]3[CH2:18][CH:17]([C:19]([OH:21])=O)[CH2:16]3)[CH:9]=2)[N:3]=1.[C:22]1([NH2:29])[C:23]([NH2:28])=[CH:24][CH:25]=[CH:26][CH:27]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C.C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[NH:29][C:19]([CH:17]1[CH2:16][N:15]([C:10]2[CH:9]=[C:8]([N:4]3[C:5]([CH3:7])=[N:6][C:2]([CH3:1])=[N:3]3)[N:13]=[C:12]([CH3:14])[N:11]=2)[CH2:18]1)=[O:21]

参加物

8

反応物 6

HCID 111,2-DichloroethaneHCID 7243O-PhenylenediamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 894937201-(6-(3,5-Dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)azetidine-3-carboxylic acid

生成物 1

HCID 89486903N-(2-Aminophenyl)-1-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)azetidine-3-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

Compound 107-2 (584 mg, 2.03 mmol), benzene-1,2-diamine (263 mg, 2.43 mmol), HOBt (465 mg, 3.04 mmol), EDC (582 mg, 3.04 mmol) and DIEA (1.77 mL, 10.1 mmol) were combined in degassed DMF (10 mL) and heated at 50° C. for 18 h. The mixture was cooled to room temperature, poured into sodium bicarbonate (200 mL, aqueous saturated) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (0-100% EtOAc (containing 10% MeOH)/hexanes), providing 107-3 as a pale green solid. MS: m/z=379.3 (M+H).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (0-100% EtOAc (containing 10% MeOH)/hexanes)

出典と根拠

ORDレコード
ord-54a19e056e72414283bace0a3ea088d2
出典データセット
uspto-grants-2016_06
特許番号
US09365562B2

反応ノート

読み込み中…