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

HRID 479694노트

반응식

HRID 479694 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
75 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4a61b287eaf94f09a18df36e9b4b5bc1
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06645990B2

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