Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate → HCID 118184928, compound

HRID 2177409Notes

Reaction equation

HRID 2177409 reaction equation
[OH:1][CH2:2][C:3]1[C:4]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)=[N:5][S:6][C:7]=1[C:8]([F:11])([F:10])[F:9].[CH3:20][C:21]1[C:26]([CH3:27])=[C:25](O)[CH:24]=[CH:23][C:22]=1[CH2:29][CH2:30][C:31]([O:33]CC)=[O:32]>>[C:16]([C:15]1[CH:18]=[CH:19][C:12]([C:4]2[C:3]([CH2:2][O:1][C:25]3[CH:24]=[CH:23][C:22]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[C:21]([CH3:20])[C:26]=3[CH3:27])=[C:7]([C:8]([F:11])([F:9])[F:10])[S:6][N:5]=2)=[CH:13][CH:14]=1)#[N:17]

Participants

3

Reactant 2

HCID 58566491Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoateHCID 118184939HCID 118184939, compound

Product 1

HCID 118184928HCID 118184928, compound

Procedure

The title compound was prepared according to the procedure described in Example 1 starting from 4-[4-(hydroxymethyl)-5-(trifluoromethyl)-1,2-thiazol-3-yl]benzonitrile, following Steps 4-6 and coupling with ethyl 3-(2,3-dimethyl-4-hydroxyphenyl)-propanoate. Upon hydrolysis, compound 264 was afforded as an off-white solid. 1H NMR (400 MHz, CDCl3) δ: 7.85 (d, J=8.4 Hz, 2H), 7.73 (d, J=8.4 Hz, 2H), 6.99 (d, J=8.6 Hz, 1H), 6.67 (d, J=8.6 Hz, 1H), 5.01 (s, 2H), 2.96 (t, J=7.8 Hz, 2H), 2.62 (t, J=7.8 Hz, 2H), 2.24 (s, 3H), 2.00 (s, 3H). 19F NMR (400 MHz, CDCl3) δ: −55.39. Mass spectrum (ESI, m/z): Calcd. for C23H19F3N2O3S, 459.0 (M−H). found 459.0.

Workup

  1. customThe title compound was prepared
  2. customUpon hydrolysis

Sources & evidence

ORD record
ord-ec9f032ddb394348aeb6ddf1c45efd34
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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