1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 71061557, compound

HRID 2201844Notes

Reaction equation

HRID 2201844 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:28])[C:10]=1[C:11]([C:13]1[C:21]2[C:16](=[C:17]([NH:22][C:23]([CH:25]3[CH2:27][CH2:26]3)=[O:24])[N:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)=[O:12])[C:5]([OH:7])=O.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[NH2:50][CH2:51][CH:52]([OH:55])[CH2:53][OH:54].C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:28])[C:10]=1[C:11]([C:13]1[C:21]2[C:16](=[C:17]([NH:22][C:23]([CH:25]3[CH2:26][CH2:27]3)=[O:24])[N:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)=[O:12])[C:5]([NH:50][CH2:51][CH:52]([OH:55])[CH2:53][OH:54])=[O:7]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 735613-Amino-1,2-propanediolHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 71061723HCID 71061723, compound

Product 1

HCID 71061557HCID 71061557, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,5-dichloro-4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)benzoic acid (50 mg, 0.11 mmol) in dimethylformamide (3 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (27.4 mg, 0.14 mmol), 1-hydroxybenzotriazole (19.37 mg, 0.14 mmol) and 3-aminopropane-1,2-diol (13 mg, 0.14 mmol) were added in one lot at room temperature. The resulting reaction mixture was stirred at room temperature for about 5 hours. Saturated aquoues sodium bicarbonate solution (20 mL) was added to quench the reaction mass. The aquoues phase was extracted with ethyl acetate and the combined organic layer dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel (100-200) column chromatography using ethyl acetate and hexane gradient elution to afford 3,5-dichloro-4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)-N-(2,3-dihydroxypropyl)benzamide (30 mg, 51.72%).

Workup

  1. customThe resulting reaction mixture
  2. customto quench the reaction mass
  3. extractionThe aquoues phase was extracted with ethyl acetate
  4. dry with materialthe combined organic layer dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel (100-200) column chromatography
  8. washethyl acetate and hexane gradient elution

Sources & evidence

ORD record
ord-805f9b59168e4b82b717003cab5c2133
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Reaction notes

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