Phenethylamine → HCID 59351279, compound

HRID 555900Notes

Reaction equation

HRID 555900 reaction equation
CN(C(ON1N=NC2C=CC=NC1=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[C:42]([C:47](O)=[O:48])=[N:43][CH:44]=[CH:45][N:46]=2)=[CH:38][CH:37]=1)=[O:35].C(N(C(C)C)CC)(C)C.[C:61]1([CH2:67][CH2:68][NH2:69])[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=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[C:42]([C:47]([NH:69][CH2:68][CH2:67][C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)=[O:48])=[N:43][CH:44]=[CH:45][N:46]=2)=[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 59351215HCID 59351215, compound

Product 1

HCID 59351279HCID 59351279, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (123 mg, 0.324 mmol) was added to a mixture of 3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazine-2-carboxylic acid (106 mg, 0.294 mmol) and diisopropylethylamine (102 μL, 0.588 mmol) in DMF (1 mL) and the mixture was stirred at RT for 10 min. 2-Phenylethylamine (55.8 μL, 0.441 mmol) was added and the mixture was stirred at RT for 1 h. The mixture was purified by chromatography on silica gel to deliver 3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)-N-phenethylpyrazine-2-carboxamide as a white solid. MS (ESI, pos. ion) m/z: 464.0 (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-36655f20928b453db3b628cb53520f40
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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