Diisopropylethylamine → HCID 76072184, compound

HRID 2200086Notes

Reaction equation

HRID 2200086 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH2:12][CH:11](NC)[CH2:10]2)=[CH:5][CH:4]=1.[F:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([N:28]([CH2:32][C:33]([OH:35])=O)[CH:29]([CH3:31])[CH3:30])(=[O:27])=[O:26])=[CH:21][CH:20]=1.[CH3:36][N:37](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:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([N:28]([CH:29]([CH3:31])[CH3:30])[CH2:32][C:33]([NH:37][CH2:36][CH:11]2[CH2:12][CH2:13][N:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:16])[F:17])=[CH:8][CH:7]=3)[CH2:10]2)=[O:35])(=[O:27])=[O:26])=[CH:21][CH:20]=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 43315056HCID 43315056, compoundHCID 60827977HCID 60827977, compound

Product 1

HCID 76072184HCID 76072184, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of crude [1-(4-trifluoromethyl-phenyl)-pyrrolidin-3-yl]-methylamine (26.6 mg, 0.11 mmol, crude) and [(4-fluoro-benzenesulfonyl)-isopropyl-amino]-acetic acid (30.0 mg, 0.11 mmol) in dichloromethane (5 mL) at 25° C. was treated with HATU (41.4 mg, 0.11 mmol). N,N-Diisopropylethylamine (28.2 mg, 0.22 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)-pyrrolidin-3-ylmethyl]-acetamide (24.2 mg, 44%) as a white solid. [MH]+=502.1.

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-0847e1a3627b4c53a1ec2a0eea794780
Source dataset
uspto-grants-2016_06
Patent number
US09359337B2

Reaction notes

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