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Diisopropylethylamine → 3-(2-Chloro-benzenesulfonyl)-cyclopentanecarboxylic acid cyanomethyl-amide

HRID 1367475
Notes
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Reaction equation

HRID 1367475 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([CH:11]1[CH2:15][CH2:14][CH:13]([C:16]([OH:18])=O)[CH2:12]1)(=[O:10])=[O:9].CCN(C(C)C)C(C)C.CN(C(O[N:36]1N=[N:43][C:38]2C=CC=N[C:37]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.NCC#N>CN(C=O)C>[C:37]([CH2:38][NH:43][C:16]([CH:13]1[CH2:14][CH2:15][CH:11]([S:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])(=[O:9])=[O:10])[CH2:12]1)=[O:18])#[N:36]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11491918Aminoacetonitrile hydrochlorideHCID 669186983-(2-Chloro-benzenesulfonyl)-cyclopentanecarboxylic acid

Product 1

HCID 72340426
3-(2-Chloro-benzenesulfonyl)-cyclopentanecarboxylic acid cyanomethyl-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-(2-chloro-benzenesulfonyl)-cyclopentanecarboxylic acid (0.25 g, 1.0 eq) in DMF (4.0 mL) was treated with DIPEA (0.22 mL, 1.5 eq) and HATU (0.39 g, 1.2 eq). The mixture was stirred at RT for 15 min, then a solution of aminoacetonitrile hydrochloride (0.12 g, 1.5 eq) and DIPEA (0.22 mL, 1.5 eq) in DMF (1 mL) was added. The resulting solution was stirred at RT overnight and then purified by preparative HPLC. The title compound was obtained as a light yellow gum (0.10 g, 37%). MS (ESI): m/z=327.1 [M+H]+.

Workup

  1. stirringThe resulting solution was stirred at RT overnight
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-6eae7c787ec64b32a25c88b4589546f0
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07893099B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes