Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 178444051, compound

HRID 923588Notes

Reaction equation

HRID 923588 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=2)=[O:11])=[CH:5][CH:4]=1.[CH2:22]([O:29][C:30]1[CH:55]=[CH:54][C:33]([CH2:34][C:35]2[NH:39][C:38]3[CH:40]=[CH:41][C:42]([CH2:44][NH:45][CH2:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])=[CH:43][C:37]=3[N:36]=2)=[CH:32][CH:31]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH2:22]([O:29][C:30]1[CH:55]=[CH:54][C:33]([CH2:34][C:35]2[NH:39][C:38]3[CH:40]=[CH:41][C:42]([CH2:44][N:45]([CH2:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C:17](=[O:19])[C:16]4[CH:15]=[CH:14][C:13]([NH:12][C:10](=[O:11])[CH2:9][C:6]5[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=5)=[CH:21][CH:20]=4)=[CH:43][C:37]=3[N:36]=2)=[CH:32][CH:31]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

7

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 18071076HCID 18071076, compoundHCID 178444050HCID 178444050, compound

Product 1

HCID 178444051HCID 178444051, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirring solution of 4-(2-(4-methoxyphenyl)acetamido)benzoic acid (142 mg, 0.498 mmol), tert-butyl 2-(((2-(4-(heptyloxy)benzyl)-1H-benzo[d]imidazol-5-yl)methyl)amino)acetate INT-48 (221, 0.475 mmol) and TEA (206 μL, 1.42 mmol) in DMF (2 mL) was added HATU (189 mg, 0.489 mmol). After stirring at room temperature for 1 h, the reaction mixture was diluted with DCM (5 mL) and NaHCO3 (15 mL). The layers were split through a hydrophobic frit and the organics evaporated. The crude product was purified by column chromatography (EA/isohexanes) to give 313 mg (88%) of tert-butyl 2-(N-((2-(4-(heptyloxy)benzyl)-1H-benzo[d]imidazol-5-yl)methyl)-4-(2-(4-methoxyphenyl)acetamido)benzamido)acetate INT-49. LCMS-ESI (m/z) calculated for C44H52N4O6: 732; found 733[M+H]+, tR=2.09 min (Method 5).

Workup

  1. customThe layers were split through a hydrophobic frit
  2. customThe crude product was purified by column chromatography (EA/isohexanes)

Sources & evidence

ORD record
ord-c165fc1ea00946b58c0f12ca2c3a7e41
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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