p-Methylphenoxyacetic acid → HCID 76901836, 화합물

HRID 1429432

반응식

HRID 1429432 반응식
[C:1]1([CH3:12])[CH:6]=[CH:5][C:4]([O:7][CH2:8][C:9]([OH:11])=O)=[CH:3][CH:2]=1.[NH2:13][CH2:14][CH:15]([OH:27])[CH2:16][N:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18]1.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:25][CH2:26][N:17]1[CH2:16][CH:15]([OH:27])[CH2:14][NH:13][C:9](=[O:11])[CH2:8][O:7][C:4]1[CH:3]=[CH:2][C:1]([CH3:12])=[CH:6][CH:5]=1

참가 물질

6

반응물 4

HCID 70329p-Methylphenoxyacetic acidHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 167907201-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol

생성물 1

HCID 76901836HCID 76901836, 화합물수율 13.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of compound 2-(p-tolyloxy)acetic acid (100 mg, 0.60 mmol), 1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol (124 mg, 0.60 mmol), BOP-Cl (183 mg, 0.72 mmol) and DIPEA (1 mL) in DCM (10 mL) was stirred at room temperature for 4 h. The solvent was removed by concentration and the crude product was purified by pre-HPLC to give the title compound (27.8 mg, yield 13.1%). 1H NMR (500 MHz, MeOD): δ 7.32-7.25 (m, 3H), 7.20 (d, J=7.2 Hz, 1H), 7.12 (d, J=8.4 Hz, 2H), 6.90 (d, J=8.8 Hz, 2H), 4.65-4.52 (br.s, 1H), 4.52 (s, 2H), 4.46-4.30 (br.s, 1H), 4.30-4.24 (m, 1H), 3.85-3.70 (br.s, 1H), 3.43 (d, J=5.6 Hz, 1H), 3.26-3.17 (m, 4H), 2.26 (s, 3H) ppm; ESI-MS (m/z): 355.2 [M+1]+.

후처리

  1. customThe solvent was removed by concentration
  2. customthe crude product was purified by pre-HPLC

출처 및 근거

ORD 기록
ord-c09b377f24fc4671b8795f2fac99c477
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940726B2

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