Diisopropylethylamine → HCID 68204542, compound

HRID 2170854Notes

Reaction equation

HRID 2170854 reaction equation
Cl.[Cl:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:5][CH:4]=1.[C:16]([O:20][C:21]([NH:23][CH2:24][C:25]1[CH:30]=[CH:29][N:28]=[C:27]([C:31](O)=[O:32])[CH:26]=1)=[O:22])([CH3:19])([CH3:18])[CH3:17].C(N(CC)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)C=O.O>[Cl:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]2[CH2:9][CH2:10][N:11]([C:31]([C:27]3[CH:26]=[C:25]([CH2:24][NH:23][C:21](=[O:22])[O:20][C:16]([CH3:18])([CH3:17])[CH3:19])[CH:30]=[CH:29][N:28]=3)=[O:32])[CH2:12][CH2:13]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 177497914-(4-Chlorophenoxy)piperidine hydrochlorideHCID 446301574-(boc-aminomethyl)pyridine-2-carboxylic acid

Product 1

HCID 68204542HCID 68204542, compoundYield 116.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 4-(4-chlorophenoxy)piperidine hydrochloride (98 mg, 0.34 mmol), 4-(((tert-butoxycarbonyl)amino)methyl)picolinic acid (100 mg, 0.34 mmol), and N,N-diisopropylethylamine (0.14 mL, 0.79 mmol) in N,N-dimethylformamide (2 mL) was add HBTU (225 mg, 0.60 mmol) at room temperature. After stirring at 60° C. for 2 hours, the mixture was poured into water (5 mL). This was extracted with ethyl acetate (5 mL) and washed with water (5 mL). The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (NH-gel, eluting with ethyl acetate) to give 177 mg (>99% yield) of the title compound as slight brown syrup.

Workup

  1. extractionThis was extracted with ethyl acetate (5 mL)
  2. washwashed with water (5 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica-gel column chromatography (NH-gel, eluting with ethyl acetate)

Sources & evidence

ORD record
ord-1cadf390f6c24297bb45e42e6b3a9773
Source dataset
uspto-grants-2015_06
Patent number
US09051296B2

Reaction notes

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