1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59811150, compound

HRID 2113626Notes

Reaction equation

HRID 2113626 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.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]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 80170N-HydroxysuccinimideHCID 81531DiisopropylethylamineHCID 69017774HCID 69017774, compound

Product 1

HCID 59811150HCID 59811150, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 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 EDCI (10.19 g, 53.16 mmol) in a solution of dry THF (100 mL) and Hunig's base (16.12 g, 125 mmol). Stir the reaction mixture overnight at room temperature. Add ethyl acetate (200 mL) was and extract the organic phase with water (3×100 mL) and brine (100 mL). Dry the organic extract over Na2SO4 and remove the solvent under reduced pressure to yield the title compound as a brown foam.

Workup

  1. extractionextract the organic phase with water (3×100 mL) and brine (100 mL)
  2. customDry the
  3. extractionorganic extract over Na2SO4
  4. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-916ec148b1684f97b6de0038de356ff2
Source dataset
uspto-grants-2008_10
Patent number
US07432275B2

Reaction notes

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