Ethanolamine → HCID 58922511, compound

HRID 639167Notes

Reaction equation

HRID 639167 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:6]([CH3:18])=[C:5]([C:19]([OH:21])=O)[CH:4]([C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=2)[C:3]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31].CN(C)C=O.[NH2:40][CH2:41][CH2:42][OH:43]>>[NH2:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:17])[F:16])[CH:9]=2)[C:6]([CH3:18])=[C:5]([C:19]([NH:40][CH2:41][CH2:42][OH:43])=[O:21])[CH:4]([C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=2)[C:3]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

4

Reactant 3

HCID 700EthanolamineHCID 6228DimethylformamideHCID 58922464HCID 58922464, compound

Product 1

HCID 58922511HCID 58922511, compound

Procedure

To a solution of 23.57 mg (0.05 mmol) of the compound of Example 60 in 100 μl dimethylformamide 16.22 mg (0.10 mmol) 1-(1H-imidazol-1-ylcarbonyl)-1H-imidazole and 12.22 mg (0.20 mmol) 2-aminoethanol are added. After stirring for 15 minutes, the reaction mixture is allowed to stand at room temperature for two days. The reaction mixture is purified by preparative HPLC (column: Agilent Zorbax Extend C18 20 mm×50 mm, 5 μm; solvent A: acetonitrile, solvent B: water+0.1% triethylamine; gradient: 0 min 10% A, 2 min 10% A, 6 min 90% A, 7 min 90% A, 7.1 min 10% A, 8 min 10% A; wavelength: 220 nm; injection volume: ca 500 μl; number of injections: 1). The product containing fractions are combined and concentrated in vacuo.

Workup

  1. waitto stand at room temperature for two days
  2. customThe reaction mixture is purified by preparative HPLC (column: Agilent Zorbax Extend C18 20 mm×50 mm, 5 μm; solvent A: acetonitrile, solvent B: water+0.1% triethylamine; gradient: 0 min 10% A, 2 min 10% A, 6 min 90% A, 7 min 90% A, 7.1 min 10% A, 8 min 10% A; wavelength: 220 nm; injection volume: ca 500 μl; number of injections: 1)
  3. additionThe product containing fractions
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4e6ca4b80f76430bb7f90c00317cf75c
Source dataset
uspto-grants-2010_04
Patent number
US07691854B2

Reaction notes

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