Ethyl 3-(4-hydroxynaphthalen-1-yl)propanoate → HCID 90418357, compound

HRID 2177197Notes

Reaction equation

HRID 2177197 reaction equation
CS([O:5][CH2:6][C:7]1[C:8]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][CH:17]=2)=[N:9][S:10][C:11]=1[C:12]([F:15])([F:14])[F:13])(=O)=O.O[C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([CH2:35][CH2:36][C:37]([O:39]CC)=[O:38])=[CH:27][CH:26]=1>>[CH2:22]([C:19]1[CH:20]=[CH:21][C:16]([C:8]2[C:7]([CH2:6][O:5][C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:28]([CH2:35][CH2:36][C:37]([OH:39])=[O:38])=[CH:27][CH:26]=3)=[C:11]([C:12]([F:15])([F:14])[F:13])[S:10][N:9]=2)=[CH:17][CH:18]=1)[CH3:23]

Participants

3

Reactant 2

HCID 58566550Ethyl 3-(4-hydroxynaphthalen-1-yl)propanoateHCID 90418592HCID 90418592, compound

Product 1

HCID 90418357HCID 90418357, compound

Procedure

The title compound was prepared according to the procedure described in Example 1 starting from (3-(4-ethylphenyl)-5-(trifluoromethyl)isothiazol-4-yl)methyl methanesulfonate following Step 5 and 6 using ethyl 3-(4-hydroxynaphthalen-1-yl)propanoate as coupling agent to afford the desired product as an off-white solid. 1H-NMR (300 MHz, CDCl3) δ 8.22 (d, J=8.1 Hz, 2H), 7.98 (d, J=8.4 Hz, 2H), 7.63 (d, J=8.4 Hz, 2H), 7.58 (t, J=7.5 Hz, 1H), 7.46 (t, J=7.5 Hz, 1H), 7.22 (d, J=8.1 Hz, 3H), 6.77 (d, J=7.8 Hz, 1H), 5.22 (s, 2H), 3.39 (t, J=7.8 Hz, 2H), 2.82 (t, J=8.1 Hz, 2H), 2.65 (q, J1=15.5 Hz, J2=7.5 Hz, 2H), 1.20 (t, J=7.8 Hz, 3H). Mass spectrum (ESI, m/z): Calcd. for C26H22F3NO3S, 486.1 (M+H). found 486.1.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-b7ea874ff3c64b6cb81efda716394397
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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