O-Phenylenediamine → HCID 25231178, compound

HRID 2093081Notes

Reaction equation

HRID 2093081 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][C:14]3[S:17][C:18]([C:20]([OH:22])=O)=[CH:19][C:13]=3[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CCN(CC)CC.CCN=C=NCCCN(C)C.[CH:41]1[CH:42]=[CH:43][C:44]2[N:49](O)N=[N:47][C:45]=2[CH:46]=1.C1(N)C=CC=CC=1N>CN(C=O)C>[NH2:47][C:45]1[CH:46]=[CH:41][CH:42]=[CH:43][C:44]=1[NH:49][C:20]([C:18]1[S:17][C:14]2[CH2:15][CH2:16][N:11]([S:8]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)(=[O:9])=[O:10])[CH2:12][C:13]=2[CH:19]=1)=[O:22]

Participants

7

Reactant 5

HCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66864421HCID 66864421, compound

Product 1

HCID 25231178HCID 25231178, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[(4-methylphenyl)sulfonyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylic acid (1.0 eq) obtained from step IV in DMF was added Et3N (2.2 eq.), EDCI (1.2 eq) and HOBt ((1.2 eq) and reaction was stirred for 1 h Phenylene diamine was added and reaction was stirred for overnight. Reaction was then quenched with water and extracted with ethyl acetate. Organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded the title compound.

Workup

  1. custom(1.2 eq) and reaction
  2. additionwas added
  3. customreaction
  4. customReaction
  5. customwas then quenched with water
  6. extractionextracted with ethyl acetate
  7. customOrganic layer was separated
  8. dry with materialdried over anhydrous Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customto afford crude product, which
  11. customon purification by column chromatography

Sources & evidence

ORD record
ord-eb43b06a22b049ddb7724a5cad055793
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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