Tetrahydrofuran → HCID 22992906, compound

HRID 1168620Notes

Reaction equation

HRID 1168620 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18](N(CC)CC)C.Cl.CN(C)[CH2:28][CH2:29][CH2:30][N:31]=C=NCC.[CH2:37]1[CH2:41]OC[CH2:38]1>CN(C)C1C=CN=CC=1>[CH3:18][C:37]1([CH3:38])[CH2:28][CH2:29][CH:30]([NH:31][C:13](=[O:15])[C:12]2[CH:11]=[CH:10][C:9]([C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:17][CH:16]=2)[CH2:41]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 691474-Benzoylbenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 22992906HCID 22992906, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

4-Benzoylbenzoic acid (0.20 mmol) and the title B compound of example 1b (0.22 mmol) were dissolved in 1 mL of THF and triethylamine (0.22 mmol) and 4-dimethylamino-pyridine (0.02 mmol) were added. 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.6 ML, 0.15 M in dichloromethane, 0.24 mmol) was added and the mixture was allowed to stand for 48 hours. Purification by preparative HPLC (YMC ODS-A S% 30×250 mm column, 50-90% methanol water with 0.10% TFA gradient over 20 minutes, 25 ml/minute flow) provided 40 mg (61%) of a white solid. C21H23NO2: m/z=322 (M+H).

Workup

  1. customPurification by preparative HPLC (YMC ODS-A S% 30×250 mm column, 50-90% methanol water with 0.10% TFA gradient over 20 minutes, 25 ml/minute flow)

Sources & evidence

ORD record
ord-cfcac4fd64ea4cfabbffd586ffee8e8c
Source dataset
uspto-grants-2003_09
Patent number
US06624309B1

Reaction notes

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