Diisopropylethylamine → HCID 67345211, compound

HRID 1669485Notes

Reaction equation

HRID 1669485 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:25]1([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.CCN(C(C)C)C(C)C.[CH:47]1([C:53]2[C:54]3[CH:55]=[CH:56][C:57]([C:77]([O:79][CH3:80])=[O:78])=[CH:58][C:59]=3[N:60]3[C:67]=2[C:66]2[CH:68]=[CH:69][CH:70]=[CH:71][C:65]=2[O:64][CH2:63][CH:62]([CH2:72][CH2:73][C:74](O)=[O:75])[CH2:61]3)[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]1>CN(C=O)C>[C:34]([O:33][C:31]([N:25]1[CH2:30][CH2:29][N:28]([C:74](=[O:75])[CH2:73][CH2:72][CH:62]2[CH2:61][N:60]3[C:59]4[CH:58]=[C:57]([C:77]([O:79][CH3:80])=[O:78])[CH:56]=[CH:55][C:54]=4[C:53]([CH:47]4[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]4)=[C:67]3[C:66]3[CH:68]=[CH:69][CH:70]=[CH:71][C:65]=3[O:64][CH2:63]2)[CH2:27][CH2:26]1)=[O:32])([CH3:37])([CH3:36])[CH3:35]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67346138HCID 67346138, compound

Product 1

HCID 67345211HCID 67345211, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

HATU (1.1 eq) was added to a stirred mixture of tert-butyl piperazine-1-carboxylate (1.1 eq), DIPEA (2.5 eq) and 3-[14-cyclohexyl-11-(methoxycarbonyl)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocin-7-yl]propanoic acid (0.03 M) in DMF under N2 at RT. The reaction was warmed at 50° C. for 10 min. The reaction was allowed to cool to RT before being partitioned between EtOAc and 1N HCl (aq). The organics were washed with 1N HCl (aq), sat. aq. NaHCO3, water and brine before being dried (Na2SO4), filtered and concentrated in vacuo. The material was taken on without further purification (88%). (ES+) m/z 630 (M+H)+; 652 (M+Na)+.

Workup

  1. temperatureto cool to RT
  2. custombefore being partitioned between EtOAc and 1N HCl (aq)
  3. washThe organics were washed with 1N HCl (aq), sat. aq. NaHCO3, water and brine
  4. dry with materialbefore being dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe material was taken on without further purification (88%)

Sources & evidence

ORD record
ord-80687a583558449fbb2819592021d728
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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