N-Methylbenzeneethanamine → HCID 57447918, compound

HRID 2101219Notes

Reaction equation

HRID 2101219 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C.[C:44]([O:48][C:49](=[O:88])[CH:50]([CH2:73][C:74]1[CH:75]=[N:76][C:77]([NH:80][C:81]([O:83][C:84]([CH3:87])([CH3:86])[CH3:85])=[O:82])=[CH:78][CH:79]=1)[CH:51]([S:63][CH2:64][C:65]1[CH:70]=[CH:69][C:68]([O:71][CH3:72])=[CH:67][CH:66]=1)[CH2:52][CH2:53][C:54]1[CH:55]=[C:56]([CH:60]=[CH:61][CH:62]=1)[C:57]([OH:59])=O)([CH3:47])([CH3:46])[CH3:45]>CN(C=O)C>[C:84]([O:83][C:81]([NH:80][C:77]1[N:76]=[CH:75][C:74]([CH2:73][CH:50]([CH:51]([S:63][CH2:64][C:65]2[CH:66]=[CH:67][C:68]([O:71][CH3:72])=[CH:69][CH:70]=2)[CH2:52][CH2:53][C:54]2[CH:62]=[CH:61][CH:60]=[C:56]([C:57]([N:2]([CH3:1])[CH2:3][CH2:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[O:59])[CH:55]=2)[C:49]([O:48][C:44]([CH3:46])([CH3:45])[CH3:47])=[O:88])=[CH:79][CH:78]=1)=[O:82])([CH3:85])([CH3:86])[CH3:87]

Participants

6

Reactant 4

HCID 11503N-MethylbenzeneethanamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69072340HCID 69072340, compound

Product 1

HCID 57447918HCID 57447918, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-methylphenethylamine (20 μL, 0.14 mmoL), HATU (55 mg, 0.15 mmoL) and iPr2EtN (46 μL, 0.26 mmoL) was added to a solution of 3-{5-tert-butoxy-4-({6-[(tert-butoxycarbonyl) amino]pyridin-3-yl}methyl)-3-[(4-methoxybenzyl)thio]-5-oxopentyl}benzoic acid (84 mg, 0.132 mmol) in DMF (2 mL) under argon at 0° C. The reaction mixture was stirred for 2 h and was then quenched with ice. Diethylether and water was added and the aqueous phase was extracted diethyl ether. The combined organic phase was dried and concentrated. Flash chromatography (heptan/EtOAc, 3:1) gave tert-butyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-3-[(4-methoxybenzyl)thio]-5-(3-{[methyl(2-phenylethyl)amino]carbonyl}phenyl)pentanoate (81 mg, 81.4%).

Workup

  1. customwas then quenched with ice
  2. additionDiethylether and water was added
  3. extractionthe aqueous phase was extracted diethyl ether
  4. customThe combined organic phase was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7279c547db114b48986da5cca5a4d0e1
Source dataset
uspto-grants-2009_08
Patent number
US07572817B2

Reaction notes

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