Triethylamine → N-(3-aminosulfonyl-4-chloro-2-hydroxyphenyl)-N'-(3-methylisoxazol-4-yl)urea

HRID 396294

반응식

HRID 396294 반응식
[CH3:1][C:2]1[C:6](C(O)=O)=[CH:5][O:4][N:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:17])C=CC=CC=1.C([N:29]([CH2:32]C)CC)C.[NH2:34][C:35]1[C:36]([OH:46])=[C:37]([S:42]([NH2:45])(=[O:44])=[O:43])[C:38]([Cl:41])=[CH:39][CH:40]=1>CN(C)C=O>[NH2:45][S:42]([C:37]1[C:36]([OH:46])=[C:35]([NH:34][C:32]([NH:29][C:6]2[C:2]([CH3:1])=[N:3][O:4][CH:5]=2)=[O:17])[CH:40]=[CH:39][C:38]=1[Cl:41])(=[O:44])=[O:43]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 45896923-Methyl-1,2-oxazole-4-carboxylic acidHCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamide

생성물 1

HCID 9968096N-(3-aminosulfonyl-4-chloro-2-hydroxyphenyl)-N'-(3-methylisoxazol-4-yl)urea수율 16%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
80 °C

실험 절차

Under Ar, the mixture of 3-methylisoxazole-4-carboxylic acid (100 mg, 0.79 mmol) in 2 mL of N,N-dimethyl-formamide was heated to 80° C. Diphenylphosphoryl azide (216 mg, 0.79 mmol) and triethyl amine (0.11 mL, 0.79 mmol) were added. The resulting mixture was heated for another 2 hours when kept temperature at 80° C. The mixture was cooled to room temperature, a solution of 3-amino-6-chloro-2-hydroxybenzenesulfonamide (176 mg, 0.79 mmol) in 1 mL of N,N-dimethyl-formamide then added. The mixture was stirred for 18 hours at room temperature. Purification upon Gilson HPLC, eluting with acetonitrile/water (10/90, v/v to 90/10, v/v, over 10 min), gave the desired product (43 mg, 16%). LC-MS (m/z) 347.0 (M+).

후처리

  1. temperatureThe resulting mixture was heated for another 2 hours when
  2. customat 80° C
  3. temperatureThe mixture was cooled to room temperature
  4. customPurification upon Gilson HPLC
  5. washeluting with acetonitrile/water (10/90, v/v to 90/10

출처 및 근거

ORD 기록
ord-413ed2c85fbc4cb4a3994e80d764e3d4
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608077B2

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