Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate → HCID 118184919, compound

HRID 2177408Notes

Reaction equation

HRID 2177408 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].[F:20][C:21]1[CH:22]=[C:23]([CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])[CH:24]=[C:25]([F:28])[C:26]=1O>>[C:16]([C:15]1[CH:18]=[CH:19][C:12]([C:4]2[C:3]([CH2:2][O:1][C:26]3[C:25]([F:28])=[CH:24][C:23]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[CH:22][C:21]=3[F:20])=[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 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoateHCID 118184939HCID 118184939, compound

Product 1

HCID 118184919HCID 118184919, 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 using ethyl 3-(3,5-difluoro-4-hydroxyphenyl)-propanoate. Upon hydrolysis, the desired compound 261 was afforded as an off-white solid. 1H NMR (300 MHz, CD3OD) δ: 7.98 (d, J=8.4 Hz, 2H), 7.87 (d, J=8.4 Hz, 2H), 6.88 (d, J=9.6 Hz, 2H), 5.23 (s, 2H), 2.87 (t, J=7.8 Hz, 2H), 2.60 (t, J=7.8 Hz, 2H). 19F NMR (300 MHz, CD3OD) δ: −56.54, −77.52, −129.65. Mass spectrum (ESI, m/z): Calcd. for C21H13F5N2O3S, 467.0 (M−H). found 466.9.

Workup

  1. customThe title compound was prepared
  2. customUpon hydrolysis

Sources & evidence

ORD record
ord-2356b9ceb53f43a48e8f58ef867ba254
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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