Cumylamine → HCID 59275384, compound

HRID 1025070Notes

Reaction equation

HRID 1025070 reaction equation
CCN(C(C)C)C(C)C.[CH2:10]([O:12][C:13]([C:15]1[C:19]2[CH:20]=[C:21]([C:30]3[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=3)[C:33]([OH:35])=O)[C:22]([N:24]([CH3:29])[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:23][C:18]=2[O:17][C:16]=1[C:39]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=1)=[O:14])[CH3:11].[C:46]1([C:52]([NH2:55])([CH3:54])[CH3:53])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[F:45][C:42]1[CH:41]=[CH:40][C:39]([C:16]2[O:17][C:18]3[CH:23]=[C:22]([N:24]([CH3:29])[S:25]([CH3:28])(=[O:27])=[O:26])[C:21]([C:30]4[CH:38]=[CH:37][CH:36]=[C:32]([C:33](=[O:35])[NH:55][C:52]([C:46]5[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=5)([CH3:54])[CH3:53])[CH:31]=4)=[CH:20][C:19]=3[C:15]=2[C:13]([O:12][CH2:10][CH3:11])=[O:14])=[CH:44][CH:43]=1

Participants

7

Reactant 4

HCID 68509CumylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59275651HCID 59275651, compound

Product 1

HCID 59275384HCID 59275384, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

DIEA (51 μL, 0.293 mmol) was added to a stirring solution of 3-(3-(ethoxycarbonyl)-2-(4-fluorophenyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)benzoic acid (50 mg, 0.098 mmol), 2-phenylpropan-2-amine (26 mg, 0.195 mmol), HATU (56 mg, 0.147 mmol) in DMF (1 mL) at 25° C. It was allowed to stir for 1 hour. The mixture was diluted with EtOAc and washed with 1M HCl, and sat NaCl. The organic phase was dried over Na2SO4, filtered and concentrated to give the titled compound (50 mg, 81%). LC-MS retention time: 1.82 min; m/z (MH+): 629. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters XBridge 5 u C18 4.6×50 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 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 5% acetonitrile/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% acetonitrile/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode.

Workup

  1. washwashed with 1M HCl
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-650fce67646d498d8f18abe80377aa95
Source dataset
uspto-grants-2014_05
Patent number
US08722688B2

Reaction notes

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