Triethylamine → HCID 58547227, compound

HRID 1850258Notes

Reaction equation

HRID 1850258 reaction equation
Cl[C:2]1[C:3]([CH:8]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.[NH2:19][CH2:20][CH2:21][CH:22]([CH3:25])[CH2:23][OH:24].[CH3:26]CN(CC)CC>CS(C)=O.O>[C:15]([O:14][C:12]([N:10]1[CH2:11][CH:8]([C:3]2[C:2]([N:19]3[CH2:26][CH2:25][CH:22]([CH2:23][OH:24])[CH2:21][CH2:20]3)=[N:7][CH:6]=[CH:5][N:4]=2)[CH2:9]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 101299114-Amino-2-methyl-1-butanolHCID 59351411Tert-butyl 3-(3-chloropyrazin-2-yl)azetidine-1-carboxylate

Product 1

HCID 58547227HCID 58547227, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of compound (7) (540 mg, 2 mmol, Preparation 2) and 4-amino-2-methyl-butan-1-ol (230 mg, 2 mmol) in DMSO (20 mL) was added Et3N (404 mg, 4 mmol). The reaction mixture was stirred at 110° C. overnight. The reaction mixture was diluted with water, extracted with EtOAc (50 mL×3). The combined organic extracts were washed with water (30 mL) and brine (30 mL), dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography (EtOAc: Petrol ether=3:1) on silica gel to give (36). (557 mg, 1.6 mmol, yield 80%).

Workup

  1. extractionextracted with EtOAc (50 mL×3)
  2. washThe combined organic extracts were washed with water (30 mL) and brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by flash column chromatography (EtOAc: Petrol ether=3:1) on silica gel

Sources & evidence

ORD record
ord-36b6ae4eb059423983649fcef72bb586
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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