Diisopropylethylamine → HCID 178496869, compound

HRID 1183806Notes

Reaction equation

NCCNC(=O)OCC1C=CC=CC=1.[N:15]([C:18](=[CH:23][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:25]=1[CH:26]=[CH:27][NH:28]2)[C:19]([O:21][CH3:22])=[O:20])=[N+]=[N-].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:23]1[C:24]2=[C:25]3[C:29]([CH:30]=[CH:31][C:32]2=[N:15][C:18]=1[C:19]([O:21][CH3:22])=[O:20])=[N:28][CH:27]=[CH:26]3

Participants

Conditions

Temperature: 25 °C

Procedure

To compound 1 (18.2 mg, 0.03 mmol) in DMF (2 mL) was added 2 (16 mg, 0.036 mmol) and HATU (14 mg, 0.036 mmol) followed by adding DIPEA (19 uL) and the reaction mixture was stirred for 7 hrs at 25° C. The solvent was removed under vacuo and the product was purified by Prep HPLC (SymmetrPrep C18, 7 μm, 19×150 mm column), eluted at 10 ml/min (0.01% TFA in water/acetonitrile) with a gradient: 10% acetonitrile in 5 min, 10% to 50% acetonitrile in 15 min, maintaining 50% acetonitrile in 5 min, 50% to 100% acetonitrile in 5 min, to give 3 (15.8 mg, 53%). MS: calcd for C59H58ClN7O9 (M+H) m/z 1044.4 found 1045.

Workup

customThe solvent was removed under vacuo
customthe product was purified by Prep HPLC (SymmetrPrep C18, 7 μm, 19×150 mm column)
washeluted at 10 ml/min (0.01% TFA in water/acetonitrile) with a gradient
wait10% acetonitrile in 5 min
wait10% to 50% acetonitrile in 15 min
temperaturemaintaining 50% acetonitrile in 5 min
wait50% to 100% acetonitrile in 5 min

Sources & evidence

ORD record: ord-328f34d682ec4ff79a1d6c949efd4406
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664407B2

Reaction notes

Loading…