Dichloromethane → HCID 89668069, compound

HRID 1753661Notes

Reaction equation

HRID 1753661 reaction equation
Cl.N1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4]C=1.[CH3:12][CH2:13][N:14]([CH2:17][CH3:18])[CH2:15][CH3:16].[CH:19]1(N=C=NC2CCCCC2)[CH2:24]CCC[CH2:20]1.Cl[CH2:35]Cl>CN(C)C1C=CN=CC=1>[CH3:4][CH:5]1[C:6]2[CH:7]=[C:16]3[C:15]4=[C:19]([CH2:24][CH2:18][CH2:17][N:14]4[CH2:13][CH2:12][CH2:35]3)[C:20]=2[O:11][C:9](=[O:10])[CH2:8]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 810974-Pyridineacetic acid hydrochloride

Product 1

HCID 89668069HCID 89668069, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

4-Pyridylacetic acid hydrochloride (58 mg, 0.34 mmol) was added with stirring to a solution of compound 9a (127 mg, 0.224 mmol) in dichloromethane (10 mL). Then Et3N (59 mg, 0.58 mmol) was added, and, after 10 min, N,N′-dicyclohexylcarbodiimide (92 mg, 0.45 mmol) and 4-dimethylaminopyridine (3.0 mg, 0.022 mmol) were added. The reaction mixture was stirred for 16 h, filtered through a plug of silica gel (using dichloromethane/ether mixture (2/1) as eluent). After evaporation of solvents, the product 10 was isolated by column chromatography (eluting with dichloromethane to dichloromethane/ether mixture, 2/1). After evaporation of solvents, compound 10 was precipitated from ether with hexane. Yield: 35 mg (23%) of light-yellow crystals. MS (ESI): m/z (positive mode, rel. int., %)=669.4 (100) [M+H]+. λabs=430 nm, λem=501 nm, ε=30700 M−1cm−1, Φfl.=0.82 (MeOH).

Workup

  1. filtrationfiltered through a plug of silica gel (using dichloromethane/ether mixture (2/1) as eluent)
  2. customAfter evaporation of solvents

Sources & evidence

ORD record
ord-c88732be6f7a4bc8b4462cc3c7a18c75
Source dataset
uspto-grants-2015_10
Patent number
US09164086B2

Reaction notes

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