Triethylamine → 6-((N-(2-(tert-butoxy)-2-oxoethyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)methyl)pyridin-3-yl 4-(heptyloxy)benzoate

HRID 923557Notes

Reaction equation

HRID 923557 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](O)=[O:18])=[CH:15][CH:14]=2)=[O:11])=[C:5]([C:22]([F:25])([F:24])[F:23])[CH:4]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:50]([O:57][C:58]1[CH:82]=[CH:81][C:61]([C:62]([O:64][C:65]2[CH:66]=[N:67][C:68]([CH2:71][NH:72][CH2:73][C:74]([O:76][C:77]([CH3:80])([CH3:79])[CH3:78])=[O:75])=[CH:69][CH:70]=2)=[O:63])=[CH:60][CH:59]=1)[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56].C(N(CC)CC)C>CN(C=O)C>[CH2:50]([O:57][C:58]1[CH:82]=[CH:81][C:61]([C:62]([O:64][C:65]2[CH:66]=[N:67][C:68]([CH2:71][N:72]([CH2:73][C:74]([O:76][C:77]([CH3:80])([CH3:79])[CH3:78])=[O:75])[C:17](=[O:18])[C:16]3[CH:15]=[CH:14][C:13]([NH:12][C:10](=[O:11])[CH2:9][C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=4[C:22]([F:25])([F:24])[F:23])=[CH:21][CH:20]=3)=[CH:69][CH:70]=2)=[O:63])=[CH:60][CH:59]=1)[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 710766706-(((2-(Tert-butoxy)-2-oxoethyl)amino)methyl)pyridin-3-yl 4-(heptyloxy)benzoateHCID 710767434-(2-(4-Methoxy-2-(trifluoromethyl)phenyl)acetamido)benzoic acid

Product 1

HCID 1176899076-((N-(2-(tert-butoxy)-2-oxoethyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)methyl)pyridin-3-yl 4-(heptyloxy)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared using General Procedure 6: To a stirred solution of 4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzoic acid INT-18 (40 mg, 0.11 mmol) in DMF (1 mL) was added HATU (45 mg, 0.11 mmol). After stirring for 1 h at room temperature, 6-(((2-(tert-butoxy)-2-oxoethyl)amino)methyl)pyridin-3-yl 4-(heptyloxy)benzoate INT-20 (61.7 mg, 0.13 mmol) was added followed by triethylamine (22.8 mg, 0.22 mmol). The reaction mixture was allowed to stir at room temperature for overnight. The final product was isolated by HPLC purification to give 6-((N-(2-(tert-butoxy)-2-oxoethyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)methyl)pyridin-3-yl 4-(heptyloxy)benzoate INT-21. LCMS-ESI (m/z) calculated for C43H48F3N3O8: 792; no m/z observed, tR=4.83 min (Method 1).

Workup

  1. customPrepared
  2. stirringto stir at room temperature for overnight

Sources & evidence

ORD record
ord-c7e960f1b63a46aea582c5240185e223
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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