Diisopropylethylamine → HCID 86679251, compound

HRID 1519662Notes

Reaction equation

HRID 1519662 reaction equation
CCN(C(C)C)C(C)C.[O:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[O:16][NH2:17].[C:18]([C:21]([N:27]([CH3:37])[C:28]([C:30]1[CH:35]=[CH:34][C:33]([I:36])=[CH:32][CH:31]=1)=[O:29])([CH3:26])[C:22]([NH:24][CH3:25])=[O:23])(O)=[O:19].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O.CN(C=O)C>[I:36][C:33]1[CH:32]=[CH:31][C:30]([C:28]([N:27]([CH3:37])[C:21]([CH3:26])([C:18]([NH:17][O:16][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][O:10]2)=[O:19])[C:22]([NH:24][CH3:25])=[O:23])=[O:29])=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71268153HCID 71268153, compound2×

Product 1

HCID 86679251HCID 86679251, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (0.11 mL) and O-(tetrahydro-2H-pyran-2-yl)hydroxylamine (24 mg) were added to a DMF (5.0 mL) solution of 1-{[2-carboxy-1-(methylamino)-1-oxopropan-2-yl](methyl)carbamoyl}-4-iodobenzene (Intermediate 11, 81 mg) and HATU (120 mg) under ice cooling, and the mixture was stirred for 2 hours at room temperature. Water was added, and the mixture was extracted with chloroform. Then, the organic layer was washed with brine, and dried over magnesium sulfate. The desiccant was filtered out, and then the solvent was distilled off under reduced pressure. The resulting residue was purified by NH type silica gel column chromatography (gradient elution with chloroform/methanol=100/0→95/5) to obtain 2-[(4-iodobenzoyl)(methyl)amino]-N,2-dimethyl-N′-(tetrahydro-2H-pyran-2-yloxy)propanediamide (Intermediate 12, light yellow oil) (59 mg, 57%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThen, the organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe desiccant was filtered out
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by NH type silica gel column chromatography (gradient elution with chloroform/methanol=100/0→95/5)

Sources & evidence

ORD record
ord-1344b9e9551046e08c266a8463323b95
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

Loading…