Diisopropylethylamine → HCID 117653647, compound

HRID 1486515Notes

Reaction equation

HRID 1486515 reaction equation
[CH3:1][C:2]([CH3:32])([CH3:31])[C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[CH:27]=[CH:26][C:20]([O:21][CH2:22][C:23](O)=[O:24])=[C:19]([CH3:28])[CH:18]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:29].[CH2:33]([O:40][NH2:41])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH2:33]([O:40][NH:41][C:23](=[O:24])[CH2:22][O:21][C:20]1[CH:26]=[CH:27][C:17]([C:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3](=[O:30])[C:2]([CH3:1])([CH3:31])[CH3:32])=[C:7]([CH3:29])[CH:8]=2)([CH2:13][CH3:14])[CH2:15][CH3:16])=[CH:18][C:19]=1[CH3:28])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 102313O-BenzylhydroxylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117653243HCID 117653243, compound

Product 1

HCID 117653647HCID 117653647, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of acid compound 6 (27.4 mg, 0.0622 mmol) in DMF (0.1 mL) was added BnONH2, (10.5 mg, 0.0653 mmol, 1.05 equiv.), followed by iPr2NEt (33 μL, 24 mg, 0.1866 mmol, 3.0 equiv.) and HBTU (25.6 mg, 0.0684 mmol, 1.1 equiv.). After 2 h, the reaction was quenched by the addition of brine and then extracted with EtOAc (×4). The combined organic phases were stirred with triethylamine resin, dried over Na2SO4 and concentrated in vacuo to give a crude product which was subsequently purified by preparative tlc (10:90 acetone/toluene). This afforded the title compound 7 (27.7 mg, 82%)

Workup

  1. customthe reaction was quenched by the addition of brine
  2. extractionextracted with EtOAc (×4)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give a crude product which
  6. customwas subsequently purified by preparative tlc (10:90 acetone/toluene)

Sources & evidence

ORD record
ord-15bdb0f8d4cc4e31bd0a77c1cb5608b9
Source dataset
uspto-grants-2016_08
Patent number
US09428447B2

Reaction notes

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