Diisopropylethylamine → HCID 90763427, compound

HRID 643063Notes

Reaction equation

HRID 643063 reaction equation
[CH2:1]([C@H:8]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C@@H:9]([OH:26])[CH2:10][N:11]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:16][CH:15]=1)[NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[B-](F)(F)F.[O:40]=C1C=CC=CN1OC(N(C)C)=[N+](C)C.C(N(C(C)C)CC)(C)C.[CH3:64][O:65][C:66]([NH:68][C@H:69]([C@@H:74]([CH3:77])[CH2:75][CH3:76])[CH2:70]C(O)=O)=[O:67]>ClCCl>[CH2:1]([C@H:8]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:31])([CH3:33])[CH3:32])[C@@H:9]([OH:26])[CH2:10][N:11]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:16][CH:15]=1)[NH:12][C:70](=[O:40])[C@@H:69]([NH:68][C:66]([O:65][CH3:64])=[O:67])[C@@H:74]([CH3:77])[CH2:75][CH3:76])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 70225858HCID 70225858, compoundHCID 86599729HCID 86599729, compound

Product 1

HCID 90763427HCID 90763427, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of Example 7B (0.36 g, 0.77 mmol) in dichloromethane (5 mL) was treated with O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TPTU) (0.344 g, 1.5 equivalent), and diisopropylethyl amine (0.4 μL, 3 equivalents) at 0° C. over 20 min. A solution of Example 3A (0.22 g, 1.5 equivalent) in dichloromethane (5 mL) was added at 0° C. and the mixture was stirred at 25° C. for 16 hrs. The mixture was washed with water, 10% sodium bicarbonate, brine, the organic layer was separated, dried over sodium sulfate, filtered and the solvents were evaporated. The crude residue was purified using 1% methanol/chloroform to give 0.37 g (76%) of the title compound.

Workup

  1. washThe mixture was washed with water, 10% sodium bicarbonate, brine
  2. customthe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvents were evaporated
  6. customThe crude residue was purified

Sources & evidence

ORD record
ord-1a68335bcdf740df943883e539d1c355
Source dataset
uspto-grants-2010_04
Patent number
US07696226B2

Reaction notes

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