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3,5-Dichlorobenzoic acid → 3,5-dichloro-N-((1-(2-(cyclopropanesulfonamido)ethyl)piperidin-4-yl)methyl)benzamide

HRID 388782
Notes
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Reaction equation

HRID 388782 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5]([OH:7])=O.[CH3:12][CH2:13]N(C(C)C)C(C)C.Cl.Cl.[NH2:23][CH2:24][CH:25]1[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][NH:33][S:34]([C:37](F)(F)F)(=[O:36])=[O:35])[CH2:27][CH2:26]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:11][C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([Cl:1])[CH:10]=1)[C:5]([NH:23][CH2:24][CH:25]1[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][NH:33][S:34]([CH:37]2[CH2:13][CH2:12]2)(=[O:36])=[O:35])[CH2:27][CH2:26]1)=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 58113,5-Dichlorobenzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67029054N-(2-(4-(aminomethyl)piperidin-1-yl)ethyl)-1,1,1-trifluoromethanesulfonamide dihydrochloride salt

Product 1

HCID 57993352
3,5-dichloro-N-((1-(2-(cyclopropanesulfonamido)ethyl)piperidin-4-yl)methyl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,5-dichlorobenzoic acid (23 mg, 0.12 mmol) in DMF (2 mL) was added DIPEA (0.1 mL, 0.6 mmol), N-(2-(4-(aminomethyl) piperidin-1-yl)ethyl)-1,1,1-trifluoromethanesulfonamide dihydrochloride salt (40 mg, 0.12 mmol) and HATU (60 mg, 0.15 mmol). The reaction mixture was stirred at room temperature overnight. The organic layer was washed with sat. NaHCO3 aq. (8 mL), dried over Na2SO4, and concentrated to give crude product which was subsequently purified by High Throughput Purification System (HiTOPs).

Workup

  1. washThe organic layer was washed with sat. NaHCO3 aq. (8 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give crude product which
  5. customwas subsequently purified by High Throughput Purification System (HiTOPs)

Sources & evidence

ORD record
ord-95ddbb57b44e497b93f652b7f4af4773
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08377968B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes