Diisopropylethylamine → HCID 67074657, compound

HRID 2042694Notes

Reaction equation

HRID 2042694 reaction equation
C(N(CC)C(C)C)(C)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[OH:32][C:33]1[CH:62]=[CH:61][C:36]([CH2:37][NH:38][C:39]2[N:44]=[C:43]([O:45][CH2:46][C:47]([F:50])([F:49])[F:48])[N:42]=[C:41]([NH:51][C:52]3[CH:60]=[CH:59][C:55]([C:56](O)=[O:57])=[CH:54][CH:53]=3)[N:40]=2)=[CH:35][CH:34]=1.[NH2:63][CH2:64][CH:65]([OH:80])[CH2:66][N:67]1[CH2:72][CH2:71][N:70]([C:73]([O:75][C:76]([CH3:79])([CH3:78])[CH3:77])=[O:74])[CH2:69][CH2:68]1>CN(C=O)C.CCOC(C)=O>[OH:80][CH:65]([CH2:64][NH:63][C:56](=[O:57])[C:55]1[CH:59]=[CH:60][C:52]([NH:51][C:41]2[N:40]=[C:39]([NH:38][CH2:37][C:36]3[CH:61]=[CH:62][C:33]([OH:32])=[CH:34][CH:35]=3)[N:44]=[C:43]([O:45][CH2:46][C:47]([F:49])([F:50])[F:48])[N:42]=2)=[CH:53][CH:54]=1)[CH2:66][N:67]1[CH2:72][CH2:71][N:70]([C:73]([O:75][C:76]([CH3:77])([CH3:79])[CH3:78])=[O:74])[CH2:69][CH2:68]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2756369(+/-)-1-amino-3-n-(4'-boc-piperazinyl)-2-propanolHCID 67073882HCID 67073882, compound

Product 1

HCID 67074657HCID 67074657, compoundYield 25.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N,N-diisopropylethylamine (0.30 g) and O-benzotriazol-1-yl-N,N,N′,N′-tetra-methyluronium tetrafluoroborate (0.44 g) were added into a solution of 4-(4-(4-hydroxybenzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoic acid (0.5 g) and tert-butyl 4-(3-amino-2-hydroxypropyl)piperazine-1-carboxylate (0.33 g) in DMF (2 mL). The mixture was stirred at room temperature for 16 hours. Then, 50 mL of EtOAc was added into the reaction mixture which was sequentially washed with water (2×20 mL) and brine (15 mL). The organic layer was dried over MgSO4 and concentrated under vacuum to give a residue which was purified by silica gel chromatography to provide tert-butyl 4-(2-hydroxy-3-(4-(4-(4-hydroxybenzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)propyl)piperazine-1-carboxylate (0.20 g).

Workup

  1. washwas sequentially washed with water (2×20 mL) and brine (15 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under vacuum
  4. customto give a residue which
  5. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-0cb97db1f75c4888b46f89a71964b08b
Source dataset
uspto-grants-2013_11
Patent number
US08586584B2

Reaction notes

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