HCID 118184908, compound → HCID 118184921, compound

HRID 2177403Notes

Reaction equation

HRID 2177403 reaction equation
[Cl:1][C:2]1[C:6]([CH2:7][OH:8])=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[S:4][N:3]=1.[F:16][C:17]1([F:34])[C:25]2[C:20](=[C:21]([CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])[CH:22]=[CH:23][C:24]=2O)[CH2:19][CH2:18]1>>[Cl:1][C:2]1[C:6]([CH2:7][O:8][C:24]2[CH:23]=[CH:22][C:21]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[C:20]3[C:25]=2[C:17]([F:34])([F:16])[CH2:18][CH2:19]3)=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[S:4][N:3]=1

Participants

3

Reactant 2

HCID 118184908HCID 118184908, compoundHCID 118184912HCID 118184912, compound

Product 1

HCID 118184921HCID 118184921, compound

Procedure

The title compound 277 was prepared according to the procedure described in Example 127, following Steps 6-7, coupling (3-chloro-5-(p-tolyl)isothiazol-4-yl)methanol with ethyl 3-(1,1-difluoro-7-hydroxy-2,3-dihydro-1H-inden-4-yl)propanoate. Upon hydrolysis, compound 277 was afforded as an off-white solid. 1H NMR (300 MHz, CD3OD) δ: 7.43 (d, J=8.1 Hz, 2H), 7.33 (d, J=7.8 Hz, 2H), 7.16 (d, J=8.1 Hz, 1H), 7.00 (d, J=8.4 Hz, 1H), 5.07 (s, 2H), 3.06 (t, J=7.8 Hz, 2H), 2.78-2.84 (m, 2H), 2.40-2.67 (m, 4H), 2.37 (s, 3H). 19F NMR (300 MHz, CD3OD) δ: −84.86. Mass spectrum (ESI, m/z): Calcd. for C23H20ClF2NO3S, 462.1 (M−H). found 462.0.

Workup

  1. customThe title compound 277 was prepared
  2. customUpon hydrolysis

Sources & evidence

ORD record
ord-558443b88f384a2e8f7754bcd058cf5e
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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