Water → HCID 59331256, compound

HRID 1882045Notes

Reaction equation

HRID 1882045 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[N:31]=[CH:30][C:29]([CH2:32][C:33](O)=[O:34])=[CH:28][CH:27]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C([N:38](CC)CC)C.Cl.CN(C)CCCN=C=NCC.O>CN(C)C=O>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[N:31]=[CH:30][C:29]([CH2:32][C:33]([NH2:38])=[O:34])=[CH:28][CH:27]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[CH:11][CH:12]=2)(=[O:5])=[O:6])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59331324HCID 59331324, compound

Product 1

HCID 59331256HCID 59331256, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]acetic acid (0.320 g) in N,N-dimethylformamide (6 mL) were added 1-hydroxybenzotriazole ammonia complex (234 mg), triethylamine (0.271 mL) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (186 mg), and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated, under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=50:50-100:0, volume ratio) and recrystallized from hexane-acetone to give the title compound (0.240 g, yield 75%) as colorless crystals. MS: 494 (MH+). melting point 151-153° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated, under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=50:50-100:0, volume ratio)
  6. customrecrystallized from hexane-acetone

Sources & evidence

ORD record
ord-b4749419f9f741699f5cfdd02eccc245
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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