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N-Hydroxysuccinimide → HCID 59811150, compound

HRID 1724831
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Reaction equation

HRID 1724831 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[C:7]([C:9]2[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:6]=[CH:5][C:4]=1[C:19]([OH:21])=[O:20].O[N:23]1[C:27](=[O:28])[CH2:26][CH2:25][C:24]1=[O:29].CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>C1COCC1.C(OCC)(=O)C>[O:29]=[C:24]1[CH2:25][CH2:26][C:27](=[O:28])[N:23]1[O:20][C:19]([C:4]1[CH:5]=[CH:6][C:7]([C:9]2[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:12]=[CH:11][N:10]=2)=[N:8][C:3]=1[NH2:2])=[O:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 80170N-HydroxysuccinimideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69017774HCID 69017774, compound

Product 1

HCID 59811150HCID 59811150, compound

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

6-Amino-3′-trifluoromethyl-[2,2′]bipyridinyl-5-carboxylic acid hydrochloride (11.33 g, 35.44 mmol), N-hydroxy-succinimide (8.15 g, 70.9 mmol), and EDCl (10.19 g, 53.16 mmol) are dissolved in a solution of dry THF (100 mL) and Hunig's base (16.12 g, 125 mmol). The reaction mixture is stirred overnight at room temperature. Ethyl acetate (200 mL) is added and the organic phase extracted with water (3×100 mL) and brine (100 mL). The organic extract is dried over Na2SO4 and the solvent removed under reduced pressure to yield the title compound as a brown foam.

Workup

  1. extractionthe organic phase extracted with water (3×100 mL) and brine (100 mL)
  2. extractionThe organic extract
  3. dry with materialis dried over Na2SO4
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-29011105759a4605ba3554e3833f0e77
Source dataset
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07488740B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes