O-Phenylenediamine → HCID 25231179, compound

HRID 2093083Notes

Reaction equation

HRID 2093083 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[O:17][C:18]([C:20](O)=[O:21])=[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[O:17][C:14]2[CH2:15][CH2:16][N:11]([S:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)(=[O:10])=[O:9])[CH2:12][C:13]=2[CH:19]=1)=[O:21]

Participants

7

Reactant 5

HCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66864147HCID 66864147, compound

Product 1

HCID 25231179HCID 25231179, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[(4-methylphenyl)sulfonyl]-4,5,6,7-tetrahydrofuro[3,2-c]pyridine-2-carboxylic acid (1.0 eq) obtained from step II 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 to reaction mass and stirred for overnight. Reaction was quenched with water and the 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 to reaction mass
  3. customReaction
  4. customwas quenched with water
  5. customthe organic layer was separated
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto afford crude product, which
  9. customon purification by column chromatography

Sources & evidence

ORD record
ord-047164bcaad843dc813857c709b8d3a4
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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