Diisopropylethylamine → HCID 68289147, compound

HRID 541227Notes

Reaction equation

HRID 541227 reaction equation
[NH2:1][C:2]1[C:3]([CH3:13])=[CH:4][C:5]([CH2:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[F:14][C:15]1([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[NH2:1][C:2]1[C:3]([CH3:13])=[CH:4][C:5]([CH2:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([N:18]1[CH2:19][CH2:20][C:15]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)([F:14])[CH2:16][CH2:17]1)=[O:9]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68288849HCID 68288849, compound2×HCID 68288856HCID 68288856, compound2×

Product 1

HCID 68289147HCID 68289147, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-amino-2-ethyl-4-methylbenzoic acid (compound 48.4, 100 mg, 0.56 mmol, 1.00 equiv), 4-(4-fluoropiperidin-4-yl)benzonitrile (compound 11.2, 140 mg, 0.69 mmol, 1.23 equiv), HBTU (320 mg, 0.84 mmol, 1.51 equiv), and DIEA (150 mg, 1.16 mmol, 2.08 equiv) in DMF (20 mL) was stirred for 48 h at room temperature. Water (30 mL) was added and the resulting mixture was extracted with 3×20 mL of ethyl acetate. The combined organic layers were washed with 1×50 mL of brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified using silica gel column chromatography with PE:EtOAc (1:1) to yield 130 mg (38%) of the title compound as a light yellow solid.

Workup

  1. extractionthe resulting mixture was extracted with 3×20 mL of ethyl acetate
  2. washThe combined organic layers were washed with 1×50 mL of brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified

Sources & evidence

ORD record
ord-d2cb686475d543269ada2641456a6964
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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