Dimethylformamide → HCID 59331386, compound

HRID 1882036Notes

Reaction equation

HRID 1882036 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13](N3C=CC=C3C3C=C(C(O)=O)C=NC=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.[CH2:35]([O:37][CH2:38][CH2:39]N)C.Cl.CN(C)[CH2:44][CH2:45][CH2:46]N=C=NCC.O[N:54]1[C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][C:57]=2[N:56]=N1.[CH3:63][N:64](C)[CH:65]=[O:66]>O.C(N(CC)CC)C>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:44]3[NH:54][C:58]([C:57]4[N:56]=[CH:59][C:60]([C:65]([NH:64][CH2:63][CH2:35][O:37][CH2:38][CH3:39])=[O:66])=[CH:61][CH:62]=4)=[CH:46][CH:45]=3)[CH2:14][CH:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 66970EthoxyethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86641958HCID 86641958, compound

Product 1

HCID 59331386HCID 59331386, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 6-(5-[(1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl]-1H-pyrrol-2-yl)pyridine-3-carboxylic acid (0.170 g) in N,N-dimethylformamide (5 mL) were added 2-ethoxyethylamine (0.056 mL), triethylamine (0.247 mL), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (101 mg) and 1-hydroxybenzotriazole (81 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=40:60-100:0, volume ratio) and recrystallized from hexane-ethyl acetate to give the title compound (0.029 g, yield 15%) as colorless crystals. MS: 552 (MH+). melting point 87-90° 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=40:60-100:0, volume ratio)
  6. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-1c56a51fef8b44809bf448d14124f93a
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

Loading…