Ethanol → 4-[3E-(5-benzo[b]thien-2-yl-2,4-dimethoxy-phenyl)-acryloyl]-benzoic acid N-methyl-D-glucamine salt

HRID 10748

반응식

HRID 10748 반응식
[S:1]1[C:5]([C:6]2[C:7]([O:27][CH3:28])=[CH:8][C:9]([O:25][CH3:26])=[C:10](/[CH:12]=[CH:13]/[C:14]([C:16]3[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=3)=[O:15])[CH:11]=2)=[CH:4][C:3]2[CH:29]=[CH:30][CH:31]=[CH:32][C:2]1=2.[NH:33]([CH2:35][C@@H:36]([C@H:38]([C@@H:40]([C@@H:42]([CH2:44][OH:45])[OH:43])[OH:41])[OH:39])[OH:37])[CH3:34].C(O)C>C1COCC1>[CH3:34][NH:33][CH2:35][C@@H:36]([C@H:38]([C@@H:40]([C@@H:42]([CH2:44][OH:45])[OH:43])[OH:41])[OH:39])[OH:37].[S:1]1[C:5]([C:6]2[C:7]([O:27][CH3:28])=[CH:8][C:9]([O:25][CH3:26])=[C:10](/[CH:12]=[CH:13]/[C:14]([C:16]3[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=3)=[O:15])[CH:11]=2)=[CH:4][C:3]2[CH:29]=[CH:30][CH:31]=[CH:32][C:2]1=2

참가 물질

5

반응물 3

HCID 702Ethanol2회HCID 8567N-Methyl-D-glucamine2회HCID 99331504-[3-(5-benzo[b]thiophen-2-yl-2,4-dimethoxy-phenyl)-E-acryloyl]-benzoic acid2회

생성물 1

HCID 865913434-[3E-(5-benzo[b]thien-2-yl-2,4-dimethoxy-phenyl)-acryloyl]-benzoic acid N-methyl-D-glucamine salt수율 63%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

4-[3E-(5-Benzo[b]thien-2-yl-2,4-dimethoxyphenyl)-acryloyl]-benzoic acid of Ex. 3 was then made into a meglumine salt by suspending the 4-[3E-(5-benzo[b]thien-2-yl-2,4-dimethoxy-phenyl)-acryloyl]-benzoic acid (4.45 g, 10 mmol) and N-methyl-D-glucamine (1.95 g, 10 mmol) in THF (100 mL). The mixture was stirred at room temperature for 5 minutes. Then, ethanol (100 mL) was added. This mixture was stirred at room temperature for 30 minutes. THF (20 mL) and ethanol (20 mL) were added and the mixture was heated slightly until it became a solution. This solution was stirred for 30 minutes and evaporated to a yellow foam. Crystallization from methanol gave the desired 4-[3E-(5-benzo[b]thien-2-yl-2,4-dimethoxy-phenyl)-acryloyl]-benzoic acid N-methyl-D-glucamine salt as a yellow solid (4 g, 63%), mp 75–80° C. (changing forms). 1H NMR (300 MHz, DMSO-d6) δ 8.39 (s, 1H), 8.14 (d, 2H), 8.02–8.10 (m, 3H), 7.94–7.98 (m, 3H), 7.86 (d, 1H), 7.36 (m, 2H), 6.89 (s, 1H), 4.06 (s, 3H), 4.04 (s, 3H), 3.94 (m, 1H), 3.71 (d, 1H), 3.61 (m, 1H), 3.39–3.55 (m, 3H), 3.04 (m, 1H), 2.95 (m, 1H), 2.54 (s, 3H). Anal. Calculated for C33H37NO10S.1.3H2O: C, 59.77; H, 6.02; N, 2.11; S, 4.84; found: C, 59.84; H, 5.75; N, 2.05; S, 4.70; Parent EIMS m/z=443 (M+).

후처리

  1. stirringThis mixture was stirred at room temperature for 30 minutes
  2. temperaturethe mixture was heated slightly until it
  3. stirringThis solution was stirred for 30 minutes
  4. customevaporated to a yellow foam
  5. customCrystallization from methanol

출처 및 근거

ORD 기록
ord-ed4268e224394520a5276dcd202bcc05
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094801B2

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