Diisopropylethylamine → HCID 76072183, compound

HRID 2200084Notes

Reaction equation

HRID 2200084 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH2:12][CH:11](NC)[CH2:10]2)=[CH:5][CH:4]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:29]([CH2:33][C:34]([OH:36])=O)[CH:30]([CH3:32])[CH3:31])(=[O:28])=[O:27])=[CH:22][CH:21]=1.[CH3:37][N:38](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.OS([O-])(=O)=O.[K+]>ClCCl>[F:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:29]([CH:30]([CH3:32])[CH3:31])[CH2:33][C:34]([NH:38][CH2:37][CH:11]2[CH2:12][CH2:13][CH2:14][N:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:17])[F:18])=[CH:8][CH:7]=3)[CH2:10]2)=[O:36])(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516920Potassium bisulfateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 60827977HCID 60827977, compoundHCID 62648620HCID 62648620, compound

Product 1

HCID 76072183HCID 76072183, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of crude [1-(4-trifluoromethyl-phenyl)-piperidin-3-yl]-methylamine (47.0 mg, 0.18 mmol, crude) and [(4-fluoro-benzenesulfonyl)-isopropyl-amino]-acetic acid (50.0 mg, 0.18 mmol) in dichloromethane (5 mL) at 25° C. was treated with HATU (69.1 mg, 0.18 mmol). N,N-Diisopropylethylamine (46.9 mg, 0.36 mmol) was added to the solution. The reaction mixture was stirred for 2 h. The reaction mixture was then poured into 0.2 M aqueous KHSO4 and extracted three times with ethyl acetate. The combined organic layers were washed three times with water and once with brine. The organic layer was then dried over magnesium sulfate, filtered and concentrated in vacuo. Flash column chromatography (50/50 hexanes/ethyl acetate) afforded 2-[(4-fluoro-benzenesulfonyl)-isopropyl-amino]-N-[1-(4-trifluoromethyl-phenyl)-piperidin-3-ylmethyl]-acetamide (50.0 mg, 53%) as a white solid. [MH]+=516.2.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic layers were washed three times with water
  3. dry with materialThe organic layer was then dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac7c00736f2c44df92cabf657e5ee972
Source dataset
uspto-grants-2016_06
Patent number
US09359337B2

Reaction notes

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