Triethylamine → 4-{4-[3-(6-Propylpyridin-2-yl)ureido]thiazol-2-yl}benzenesulfonamide

HRID 460250ノート

反応式

HRID 460250 の反応式
[S:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[C:14](C(O)=O)[N:15]=2)=[CH:7][CH:6]=1)(=[O:4])(=[O:3])[NH2:2].CC[N:21]([CH2:24]C)CC.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])=CC=1.[CH2:43]([C:46]1[N:51]=[C:50]([NH2:52])[CH:49]=[CH:48][CH:47]=1)[CH2:44][CH3:45]>C1COCC1.O.CCOC(C)=O>[CH2:43]([C:46]1[N:51]=[C:50]([NH:52][C:24](=[O:33])[NH:21][C:14]2[N:15]=[C:11]([C:8]3[CH:7]=[CH:6][C:5]([S:1]([NH2:2])(=[O:3])=[O:4])=[CH:10][CH:9]=3)[S:12][CH:13]=2)[CH:49]=[CH:48][CH:47]=1)[CH2:44][CH3:45]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 30163096-Propylpyridin-2-amineHCID 187720852-(p-Sulfamoylphenyl)thiazole-4-carboxylic acid

生成物 1

HCID 187717504-{4-[3-(6-Propylpyridin-2-yl)ureido]thiazol-2-yl}benzenesulfonamide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
75 °C

実験手順

In an oven-dried, 50-mL, round-bottomed flask were placed 2-(p-sulfamoylphenyl)thiazole-4-carboxylic acid (250 mg, 0.82 mmol), molecular sieves (800 mg) in THF (20 mL). To this mixture was added Et3N (0.23 mL, 1.64 mmol), followed by DPPA (0.28 mL, 1.28 mmol). The reaction was stirred for 5 min, then 6-propylpyridine-2-amine (280 mg, 2.06 mmol) was added. The suspension was heated to 75° C. for 14 h, cooled to RT, diluted with H2O (10 mL) and EtOAc (150 mL), and filtered to remove molecular sieves. The filtrate was concentrated in vacuo to give the crude product as a yellow solid which was filtered, washed with H2O (3×10 mL), EtOAc (1×10 mL) and Et2O (3×10 mL) to afford the title compound as a yellow solid. MS m/z: 418 (M+H). Calc'd for C18H19N5O3S2: 417.09.

後処理

  1. temperaturecooled to RT
  2. filtrationfiltered
  3. customto remove molecular sieves
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give the crude product as a yellow solid which
  6. filtrationwas filtered
  7. washwashed with H2O (3×10 mL), EtOAc (1×10 mL) and Et2O (3×10 mL)

出典と根拠

ORDレコード
ord-c1f2f9d03f4148bba2c3b9cc5e7d5043
出典データセット
uspto-grants-2007_03
特許番号
US07196104B2

反応ノート

読み込み中…