1-Hydroxybenzotriazole → N-[2-methyl-5-(3-morpholinobenzamido)phenyl]-3-tetrahydrofuran-3-yloxybenzamide

HRID 1369556노트

반응식

HRID 1369556 반응식
Cl.CN(C)CCCN=C=NCC.[O:13]1[CH2:17][CH2:16][CH:15]([O:18][C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22]([OH:24])=O)[CH2:14]1.ON1C2C=CC=CC=2N=N1.[NH2:38][C:39]1[CH:40]=[C:41]([NH:46][C:47](=[O:60])[C:48]2[CH:53]=[CH:52][CH:51]=[C:50]([N:54]3[CH2:59][CH2:58][O:57][CH2:56][CH2:55]3)[CH:49]=2)[CH:42]=[CH:43][C:44]=1[CH3:45]>CN(C=O)C.O>[CH3:45][C:44]1[CH:43]=[CH:42][C:41]([NH:46][C:47](=[O:60])[C:48]2[CH:53]=[CH:52][CH:51]=[C:50]([N:54]3[CH2:55][CH2:56][O:57][CH2:58][CH2:59]3)[CH:49]=2)=[CH:40][C:39]=1[NH:38][C:22](=[O:24])[C:21]1[CH:25]=[CH:26][CH:27]=[C:19]([O:18][CH:15]2[CH2:16][CH2:17][O:13][CH2:14]2)[CH:20]=1

참가 물질

7

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11301391N-(3-amino-4-methylphenyl)-3-morpholinobenzamideHCID 222910893-(Tetrahydrofuran-3-yloxy)benzoic acid

생성물 1

HCID 22291058N-[2-methyl-5-(3-morpholinobenzamido)phenyl]-3-tetrahydrofuran-3-yloxybenzamide수율 63.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.165 g) was added to a stirred mixture of 3-(tetrahydrofuran-3-yloxy)benzoic acid (0.15 g), 1-hydroxybenzotriazole (0.146 g) and DMF (5 ml) which had been cooled to 0° C. The reaction mixture was stirred at 0° C. for 5 minutes and a solution of N-(3-amino-4-methylphenyl)-3-morpholinobenzamide (0.224 g) in DMF (1 ml) was added. The reaction mixture was allowed to come to ambient temperature and was stirred for 16 hours. The reaction mixture was poured into water and the resultant solid was isolated and purified by column chromatography on silica using a 99:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the title compound (0.228 g); NMR Spectrum: (DMSOd6) 1.99 (m, 1H), 2.18 (s, 3H), 2.25 (m, 1H), 3.17 (t, 4H), 3.72 (t, 4H), 3.88 (m, 4H), 5.13 (m, 1H), 7.11 (m, 2H), 7.21 (d, 1H), 7.39 (m, 5H), 7.56 (m, 2H), 7.79 (m, 2H), 9.83 (s, 1H), 10.11 (s, 1H); Mass Spectrum: M+H+502.

후처리

  1. customto come to ambient temperature
  2. stirringwas stirred for 16 hours
  3. customthe resultant solid was isolated
  4. custompurified by column chromatography on silica using
  5. additiona 99:1 mixture of methylene chloride and methanol as eluent

출처 및 근거

ORD 기록
ord-b4972646a5fc4f4dbc4ba5cadbbc8dc6
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06579872B1

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