Phenethylamine → HCID 59326842, compound

HRID 410331Notes

Reaction equation

HRID 410331 reaction equation
CN(C(ON1N=N[C:11]2[CH:12]=[CH:13][CH:14]=[N:15][C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=[C:26]1[C:34]([C:36]1[CH:51]=[CH:50][C:39]([O:40][C:41]2[N:49]=[CH:48][CH:47]=[CH:46][C:42]=2[C:43](O)=[O:44])=[CH:38][CH:37]=1)=[O:35].[CH:52]([N:55](C(C)C)CC)(C)[CH3:53].C1C=CC(CCN)=CC=1>CN(C=O)C>[NH:27]1[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[N:25]=[C:26]1[C:34]([C:36]1[CH:37]=[CH:38][C:39]([O:40][C:41]2[N:49]=[CH:48][CH:47]=[CH:46][C:42]=2[C:43]([NH:55][CH2:52][CH2:53][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][N:15]=2)=[O:44])=[CH:50][CH:51]=1)=[O:35]

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59326812HCID 59326812, compound

Product 1

HCID 59326842HCID 59326842, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (122 mg, 0.321 mmol) was added to a mixture of 2-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)nicotinic acid (105 mg, 0.292 mmol) and diisopropylethylamine (102 μL, 0.584 mmol) in DMF (1 mL) and the mixture was stirred at RT for 10 min. 2-Phenethylamine (55.4 μL, 0.438 mmol) was added, and the mixture was stirred at RT for 1 h. The mixture was purified by chromatography on silica gel to deliver 2-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)-N-phenethylnicotinamide as an off-white solid. MS (ESI, pos. ion) m/z: 463.1 (M+1). IC50 (uM) +.

Workup

  1. stirringthe mixture was stirred at RT for 1 h
  2. customThe mixture was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-655075fc6475430497c72cb71ef3bd8b
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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