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

HRID 44032Notes

Reaction equation

HRID 44032 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, 3 H), 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-9bb239afe4594fedb655cd3ac5fb0178
Source dataset
uspto-grants-2013_09
Patent number
US08536338B2

Reaction notes

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