4-(2-Aminoethyl)thiomorpholine → HCID 59730358, compound

HRID 130992Notes

Reaction equation

HRID 130992 reaction equation
[F:1][C:2]1[CH:17]=[C:16]([CH:18]=O)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([NH2:13])=[O:12])=[N:9][CH:10]=1.[N:20]1([CH2:26][CH2:27][NH2:28])[CH2:25][CH2:24][S:23][CH2:22][CH2:21]1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:17]=[C:16]([CH2:18][NH:28][CH2:27][CH2:26][N:20]2[CH2:25][CH2:24][S:23][CH2:22][CH2:21]2)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([NH2:13])=[O:12])=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 27732004-(2-Aminoethyl)thiomorpholineHCID 4311764Sodium borohydrideHCID 597299375-(2-Fluoro-4-formylphenoxy)pyridine-2-carboxamide

Product 1

HCID 59730358HCID 59730358, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Place 5-(2-fluoro-4-formylphenoxy)pyridine-2-carboxamide (Example 403, Part B) (0.650 g, 2.50 mmol), 2-thiomorpholin-4-ylethylamine (0.402 g, 2.75 mmol) and 3 {acute over (Å)} molecular sieves in a vial. Add methanol (12 mL), cap and stir overnight. Add NaBH4 (slight excess) and stir until the gasses stop evolving. Load the reaction mixture directly onto a 25 g ISCO® pre-load column. Dry the column in a vacuum oven at room temperature. Purify by eluting through a 40 g ISCO® column with 0% to 30% (2.0 M NH3 in methanol) in ethyl acetate to give the title compound (0.792 g, 81%): TOF MS ES+ 391.2 (M+H)+, HRMS calcd for C19H24N4O2FS 391.1604 (M+H)+, found 391.1594, time 0.48 min; HPLC [YMC-Pro pack C-18 (150×4.6 mm, S-5 microm), 0.05% TFA/acetonitrile in 0.05% TFA/water at 1.0 mL/min, 10-20% over 5 min, 20-95% over 18], tR=6.7 min, 100% purity.

Workup

  1. customDry the column in a vacuum oven at room temperature
  2. customPurify
  3. washby eluting through a 40 g ISCO® column with 0% to 30% (2.0 M NH3 in methanol) in ethyl acetate

Sources & evidence

ORD record
ord-7dabf6237170425b8f2de351b848f748
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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