5-tert-Butylisophthalic acid → HCID 67169759, compound

HRID 2170857Notes

Reaction equation

HRID 2170857 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]([C:20]1[CH:21]=[C:22]([C:29](O)=[O:30])[CH:23]=[C:24]([CH:28]=1)[C:25]([OH:27])=[O:26])([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>[C:16]([C:20]1[CH:28]=[C:24]([CH:23]=[C:22]([C:29]([N:11]2[CH2:10][CH2:9][CH:8]([O:7][C:6]3[CH:14]=[CH:15][C:3]([Cl:2])=[CH:4][CH:5]=3)[CH2:13][CH2:12]2)=[O:30])[CH:21]=1)[C:25]([OH:27])=[O:26])([CH3:19])([CH3:17])[CH3:18]

Participants

7

Reactant 4

HCID 753795-tert-Butylisophthalic acidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 177497914-(4-Chlorophenoxy)piperidine--hydrogen chloride (1/1)

Product 1

HCID 67169759HCID 67169759, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 4-(4-chlorophenoxy)piperidine hydrochloride (100 mg, 0.40 mmol), 5-(tert-butyl)isophthalic acid (358 mg, 1.61 mmol), and N,N-diisopropylethylamine (0.28 mL, 1.61 mmol) in N,N-dimethylformamide (3 mL) was add HBTU (183 mg, 0.48 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 (eluting with dichloromethane/methanol=7:1) to give 121 mg (72% yield) of the title compound as a white solid.

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 (eluting with dichloromethane/methanol=7:1)

Sources & evidence

ORD record
ord-e988219f2f014492b0c641ee65198991
Source dataset
uspto-grants-2015_06
Patent number
US09051296B2

Reaction notes

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