Diisopropylethylamine → HCID 178525131, compound

HRID 1804660Notes

Reaction equation

HRID 1804660 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[C:10]([N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]1[C:26](O)=O)([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH2:13]([O:12][C:10]([N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]1[C:26]1[NH:8][C:5]2[CH:6]=[CH:7][C:2]([I:1])=[CH:3][C:4]=2[N:9]=1)=[O:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 688345(S)-1-N-Cbz-Pipecolinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 112070494-Iodobenzene-1,2-diamine

Product 1

HCID 178525131HCID 178525131, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 4-iodo-benzene-1,2-diamine (1.5 g, 6.4 mmol) and (S)-N-Cbz-2-piperidine-carboxylic acid (available commercially at Aldrich) (1.7 g, 6.4 mmol) in DMF (20 mL) at 0° C. is added DIPEA (3.3 mL, 19.2 mmol) followed by HATU (3.0 g, 7.69 mmol). The reaction mixture is stirred at 0° C., brought to room temperature and stirred overnight. The reaction mixture is than concentrated in vacuum and the residue is dissolved in AcOH (15 mL) and stirred at 60° C. for 4 hours. The mixture is concentrated in vacuum and the residue is dissolved in EtOAc and washed with water, 1N HCl and brine, dried over sodium sulfate and concentrated in vacuum. The residue is purified by flash column chromatography on silica gel (MeOH/DCM 0% to 20%) to give the title compound (1.4 g, 47%).

Workup

  1. custombrought to room temperature
  2. stirringstirred overnight
  3. concentrationthan concentrated in vacuum
  4. dissolutionthe residue is dissolved in AcOH (15 mL)
  5. stirringstirred at 60° C. for 4 hours
  6. concentrationThe mixture is concentrated in vacuum
  7. dissolutionthe residue is dissolved in EtOAc
  8. washwashed with water, 1N HCl and brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated in vacuum
  11. customThe residue is purified by flash column chromatography on silica gel (MeOH/DCM 0% to 20%)

Sources & evidence

ORD record
ord-9620d49872f44f72be3f3fa184eb4367
Source dataset
uspto-grants-2013_01
Patent number
US08354419B2

Reaction notes

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