Diisopropylethylamine → HCID 68510636, compound

HRID 1714049Notes

Reaction equation

HRID 1714049 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]([OH:11])=O)[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.FC(F)(F)C([O-])=O.[C:52]([C:55]1[CH:56]=[CH:57][C:58]2[C:59]([CH:75]3[CH2:80][CH2:79][CH2:78][CH2:77][CH2:76]3)=[C:60]3[C:67]4[CH:68]=[CH:69][C:70]([F:72])=[CH:71][C:66]=4[CH2:65][NH2+:64][CH2:63][CH2:62][N:61]3[C:73]=2[CH:74]=1)([OH:54])=[O:53]>C(Cl)Cl.CN(C=O)C>[CH:75]1([C:59]2[C:58]3[CH:57]=[CH:56][C:55]([C:52]([OH:54])=[O:53])=[CH:74][C:73]=3[N:61]3[CH2:62][CH2:63][N:64]([C:9](=[O:11])[CH2:8][N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]4)[CH2:65][C:66]4[CH:71]=[C:70]([F:72])[CH:69]=[CH:68][C:67]=4[C:60]=23)[CH2:76][CH2:77][CH2:78][CH2:79][CH2:80]1

Participants

7

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 2762732(4-Methylpiperazin-1-yl)acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86604969HCID 86604969, compound

Product 1

HCID 68510636HCID 68510636, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3 eq of (4-methylpiperazin-1-yl)acetic acid in DCM (0.2 M), 4 eq of DIPEA and 2 eq of HATU were added and the mixture stirred at RT for 1 h. Then a solution of 1 eq of 11-carboxy-14-cyclohexyl-3-fluoro-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocin-6-ium trifluoroacetate in DMF (0.06 M) and 1 eq of DIPEA was added and the mixture stirred at RT overnight. Volatiles were removed in vacuo. The crude was then purified by automated RP-MS-HPLC (stationary phase: column Waters SYMMETRY prep. C18, 7 μm, 19×300 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA). Fractions containing the pure compound were combined and freeze dried to afford the title compound as a white powder (51%).

Workup

  1. stirringthe mixture stirred at RT overnight
  2. customVolatiles were removed in vacuo
  3. customThe crude was then purified by automated RP-MS-HPLC (stationary phase: column Waters SYMMETRY prep. C18, 7 μm, 19×300 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA)
  4. additionFractions containing the pure compound
  5. customfreeze dried

Sources & evidence

ORD record
ord-3dceba25206545a3996eafb3f2fcf81d
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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