Diisopropylethylamine → HCID 178496869, compound

HRID 1183808Notes

Reaction equation

HRID 1183808 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-].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.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

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2794257Benzyl N-(2-aminoethyl)carbamateHCID 72253810methyl 2-azido-3-(1H-indol-4-yl)acrylate

Product 1

HCID 178496869HCID 178496869, compoundYield 338.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 1 (47 mg, 0.06 mmol), 2 (40 mg, 0.078 mmol) and BOP (34.5 mg, 0.078 mmol) in DMF (3 ml) was treated with DIPEA (68 uL). The reaction mixture was stirred at 25° C. for 30 min. The solvent was removed and was further dried in high vacuo for 4 h. The solvent was removed under vacuo and the crude 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 (56 mg, 85%). MS: calcd for C56H54BrN9O8 (M+H) m/z 1060.33 found 1060.44.

Workup

  1. customThe solvent was removed
  2. customwas further dried in high vacuo for 4 h
  3. customThe solvent was removed under vacuo
  4. customthe crude product was purified by Prep HPLC (SymmetrPrep C18, 7 μm, 19×150 mm column)
  5. washeluted at 10 ml/min (0.01% TFA in water/acetonitrile) with a gradient
  6. wait10% acetonitrile in 5 min
  7. wait10% to 50% acetonitrile in 15 min
  8. temperaturemaintaining 50% acetonitrile in 5 min
  9. wait50% to 100% acetonitrile in 5 min

Sources & evidence

ORD record
ord-58143aad63c849c1a0153b6062a05d10
Source dataset
uspto-grants-2014_03
Patent number
US08664407B2

Reaction notes

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