Tert-Butylamine → 5-(3-(tert-butylcarbamoyl)phenyl)-2-(4-fluorophenyl)-N-methylbenzo[b]thiophene-3-carboxamide

HRID 219352Notes

Reaction equation

HRID 219352 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[CH:14][C:15]([C:17]4[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=4)[C:20](O)=[O:21])=[CH:16][C:10]=3[C:9]=2[C:26](=[O:29])[NH:27][CH3:28])=[CH:4][CH:3]=1.[CH3:30][C:31]([NH2:34])([CH3:33])[CH3:32]>>[C:31]([NH:34][C:20]([C:19]1[CH:18]=[C:17]([C:15]2[CH:14]=[CH:13][C:11]3[S:12][C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[C:9]([C:26]([NH:27][CH3:28])=[O:29])[C:10]=3[CH:16]=2)[CH:25]=[CH:24][CH:23]=1)=[O:21])([CH3:33])([CH3:32])[CH3:30]

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 592338473-(2-(4-Fluorophenyl)-3-(methylcarbamoyl)benzo[b]thiophen-5-yl)benzoic acid

Product 1

HCID 592337135-(3-(tert-butylcarbamoyl)phenyl)-2-(4-fluorophenyl)-N-methylbenzo[b]thiophene-3-carboxamide

Procedure

5-(3-(tert-butylcarbamoyl)phenyl)-2-(4-fluorophenyl)-N-methylbenzo[b]thiophene-3-carboxamide was prepared from 3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)benzo[b]thiophen-5-yl)benzoic acid (0.075 g, 0.15 mmol) and 2-methylpropan-2-amine (0.016 g, 0.22 mmol). 1H NMR (500 MHz, DMSO-D6) δ ppm 8.42 (s, 1H), 8.16 (s, 1H), 8.07 (s, 1H), 7.96 (s, 2H), 7.82 (s, 3H), 7.66 (s, 2H), 7.57 (s, 1H), 7.37 (s, 2H), 2.78 (s, 3H), 1.42 (s, 9H). LCMS: retention time: 3.218 min. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna, 10 micron, C18, 4.6×30 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 4 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% CH3OH/90% H2O/10 mM TFA and solvent B was 10% H2O/90% CH3OH/10 mM TFA. MS data was determined using a Micromass Platform for LC in electrospray mode. m/z 461 (MH+).

Workup

  1. customequipped with a Phenomenex-Luna, 10 micron, C18, 4.6×30 mm column
  2. washThe elution conditions
  3. customa gradient time of 3 min
  4. customa hold time of 1 min
  5. customan analysis time of 4 min where solvent A was 10% CH3OH/90% H2O/10 mM TFA and solvent B

Sources & evidence

ORD record
ord-aed6b6af91a349acaedbd952710852c7
Source dataset
uspto-grants-2012_06
Patent number
US08198449B2

Reaction notes

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