4-Methoxyphenoxyacetic acid → HCID 90241398, compound

HRID 1777113Notes

Reaction equation

HRID 1777113 reaction equation
CO[C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][C:9]([OH:11])=O)=[CH:5][CH:4]=1.[NH2:14][CH2:15][CH:16]([OH:28])[CH2:17][N:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19]1.C1N(P(Cl)(N2C(=O)[O:40][CH2:39][CH2:38]2)=O)C(=O)OC1.CC[N:46](C(C)C)C(C)C>C(Cl)Cl>[C:39]([NH:46][C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][C:9]([NH:14][CH2:15][CH:16]([OH:28])[CH2:17][N:18]2[CH2:27][CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19]2)=[O:11])=[CH:12][CH:13]=1)(=[O:40])[CH3:38]

Participants

6

Reactant 4

HCID 746494-Methoxyphenoxyacetic acidHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 167907201-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol

Product 1

HCID 90241398HCID 90241398, compoundYield 3.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of compound 2-(4-methoxyphenoxy)acetic acid (100 mg, 0.51 mmol), 1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol (132 mg, 0.51 mmol), BOP-Cl (156 mg, 0.61 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 (7.8 mg, yield: 3.8%). 1H NMR (500 MHz, MeOD): δ 7.45 (d, d, J=8.8 Hz, 2H), 7.11-7.05 (m, 3H), 7.02-7.00 (m, 1H), 6.88 (d, J=8.8 Hz, 2H), 4.50 (s, 2H), 4.01-3.98 (m, 1H), 3.66 (d, J=3.2 Hz, 2H), 3.41 (dd, J=0.8, 6.0 Hz, 2H), 2.89-2.87 (m, 2H), 2.80-2.76 (m, 2H), 2.55 (d, J=6.0 Hz, 2H), 2.08 (s, 3H) ppm; ESI-MS (m/z): 398.2 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-ea3fbabbd7e446bda40c47e761e4cd41
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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