Diisopropylethylamine → 2-(4-{(E)-2-Acetylamino-3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acryloylamino}-butoxy)-6-benzyloxybenzoic Acid Methyl Ester

HRID 660631Notes

Reaction equation

HRID 660631 reaction equation
[C:1]([NH:4]/[C:5](=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:20][C:19](=[O:21])[NH:18][S:17]2(=[O:23])=[O:22])=[C:12]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:11]=1)/[C:6](O)=[O:7])(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:65][O:66][C:67](=[O:88])[C:68]1[C:73]([O:74][CH2:75][C:76]2[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=2)=[CH:72][CH:71]=[CH:70][C:69]=1[O:82][CH2:83][CH2:84][CH2:85][CH2:86][NH2:87]>CN(C=O)C>[CH3:65][O:66][C:67](=[O:88])[C:68]1[C:73]([O:74][CH2:75][C:76]2[CH:77]=[CH:78][CH:79]=[CH:80][CH:81]=2)=[CH:72][CH:71]=[CH:70][C:69]=1[O:82][CH2:83][CH2:84][CH2:85][CH2:86][NH:87][C:6](=[O:7])/[C:5](/[NH:4][C:1](=[O:3])[CH3:2])=[CH:9]\[C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:20][C:19](=[O:21])[NH:18][S:17]2(=[O:23])=[O:22])=[C:12]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:11]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 684293722-(4-Aminobutoxy)-6-benzyloxybenzoic Acid Methyl EsterHCID 68840076(E)-2-Acetylamino-3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acrylic Acid

Product 1

HCID 688378762-(4-{(E)-2-Acetylamino-3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acryloylamino}-butoxy)-6-benzyloxybenzoic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of (E)-2-acetylamino-3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acrylic acid (260 mg, 0.58 mmol) in DMF (10 mL) is added diisopropylethylamine (0.11 mL, 0.64 mmol) and HATU (243 mg, 0.64 mmol). The mixture is stirred at RT for 10 min then a solution of 2-(4-aminobutoxy)-6-benzyloxybenzoic acid methyl ester (Example 110, step C) (286 mg, 0.87 mmol) in DMF (1 mL) is added and stirring is continued for 18 h. The solvent is removed under reduced pressure to give the title compound which is used directly in the next step.

Workup

  1. stirringstirring
  2. waitis continued for 18 h
  3. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-a17a1946203e4388893dfd76512db59d
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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