Ethanolamine → HCID 11123387, compound

HRID 1835103Notes

Reaction equation

HRID 1835103 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[N:11]([CH3:28])[C:12]2[C:13]([N:27]=1)=[C:14]([CH:25]=O)[CH:15]=[C:16]1[C:21]=2[C:20](=[O:22])[NH:19][C:18]([CH3:23])=[C:17]1[CH3:24].[CH2:29]([CH2:31][NH2:32])[OH:30].[BH3-]C#N.[Na+]>CO>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[NH:9][C:10]1[N:11]([CH3:28])[C:12]2[C:21]3[C:20](=[O:22])[NH:19][C:18]([CH3:23])=[C:17]([CH3:24])[C:16]=3[CH:15]=[C:14]([CH2:25][NH:32][CH2:31][CH2:29][OH:30])[C:13]=2[N:27]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 5003444Sodium cyanoborohydrideHCID 10949733HCID 10949733, compound

Product 1

HCID 11123387HCID 11123387, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of the product of Example 23 (30 mg, 0.07 mmol) in MeOH (5 mL) was treated with ethanolamine (44 μL, 0.72 mmol) and NaBH3CN (14 mg, 0.22 mmol), and stirred at room temperature for 16 h. The resulting mixture was concentrated and the residue was diluted with water. The precipitated solid was filtered to give the title compound (12 mg, 36%). mp decomp. above 250° C.; MS (CI) 460 (MH+).

Workup

  1. concentrationThe resulting mixture was concentrated
  2. additionthe residue was diluted with water
  3. filtrationThe precipitated solid was filtered

Sources & evidence

ORD record
ord-254880a6b4fe4225970d5e8f706c5600
Source dataset
uspto-grants-2004_08
Patent number
US06770639B2

Reaction notes

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