Diisopropylethylamine → (+/-)-{4-Chloro-2-[2-(2-methoxy-benzylthiocarbamoyl)-1,2,3,4-tetrahydro-isoquinolin-1-yl]-phenoxy}-acetic acid

HRID 2036203

반응식

HRID 2036203 반응식
Cl.C([O:4][C:5](=[O:25])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17][NH:16]1)C.C(N(C(C)C)C(C)C)C.[CH3:35][O:36][C:37]1[CH:46]=[CH:45][CH:44]=[CH:43][C:38]=1[CH2:39][N:40]=[C:41]=[S:42]>C(Cl)Cl>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:5]([OH:4])=[O:25])=[C:9]([CH:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][N:16]2[C:41](=[S:42])[NH:40][CH2:39][C:38]2[CH:43]=[CH:44][CH:45]=[CH:46][C:37]=2[O:36][CH3:35])[CH:10]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 1402562-Methoxybenzyl isothiocyanateHCID 66653750(+/-)-[4-Chloro-2-(1,2,3,4-tetrahydro-isoquinolin-1-yl)-phenoxy]-acetic acid ethyl ester hydrochloride

생성물 1

HCID 86682579(+/-)-{4-Chloro-2-[2-(2-methoxy-benzylthiocarbamoyl)-1,2,3,4-tetrahydro-isoquinolin-1-yl]-phenoxy}-acetic acid

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of (±)-[4-chloro-2-(1,2,3,4-tetrahydro-isoquinolin-1-yl)-phenoxy]-acetic acid ethyl ester hydrochloride (76 mg, 0.20 mmol, 1.0 eq.) and N-ethyldiisopropylamine (42 μL, 0.24 mmol, 1.2 eq) in DCM (2 mL), 2-methoxybenzyl isothiocyanate (36 mg, 0.20 mmol, 1.0 eq.) was added. The resulting mixture was stirred at r.t. for 19 hours. The mixture was diluted with DCM (20 mL), washed with 10% aq. AcOH (2×5 mL) and with sat. aq. NaCl (1×5 mL). The org. layer was concentrated in vacuo. The residue was dissolved in DMF (1 mL). 1M aq. NaOH soln. (0.5 mL) was added. The mixture was stirred at r.t. for 7 hours. The solution was carefully neutralized with formic acid (0.5 mL), filtered, and purified by prep. HPLC (column: Waters X-bridge, 30×75 mm, 10 um, UV/MS, acidic conditions) to give the desired acid as a white solid.

후처리

  1. washwashed with 10% aq. AcOH (2×5 mL) and with sat. aq. NaCl (1×5 mL)
  2. concentrationlayer was concentrated in vacuo
  3. dissolutionThe residue was dissolved in DMF (1 mL)
  4. addition(0.5 mL) was added
  5. stirringThe mixture was stirred at r.t. for 7 hours
  6. filtrationfiltered
  7. custompurified by prep

출처 및 근거

ORD 기록
ord-d548314e33bf465ba5d30e2eeeff4fc5
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575158B2

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