4-Methylmorpholine → HCID 22958561, compound

HRID 637005Notes

Reaction equation

HRID 637005 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[C:12]([OH:14])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:15][C:16]1[C:25]2[C:20](=[CH:21][C:22]([CH2:26][NH2:27])=[CH:23][CH:24]=2)[CH:19]=[CH:18][N:17]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[NH2:15][C:16]1[C:25]2[C:20](=[CH:21][C:22]([CH2:26][NH:27][C:12]([C@@H:9]3[CH2:10][CH2:11][N:8]3[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:14])=[CH:23][CH:24]=2)[CH:19]=[CH:18][N:17]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2734495(2S)-1-((tert-butoxy)carbonyl)azetidine-2-carboxylic acidHCID 221697756-(Aminomethyl)isoquinolin-1-amine

Product 1

HCID 22958561HCID 22958561, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.00 g 1-Tert.butoxycarbonyl-azetidin-2(S)-carboxylic acid, 1.70 g 1-amino-6-aminomethyl-isoquinolin, 3.50 g TBTU were dissolved in 40 mL DMF. 3.55 mL N-methylmorpholin was added slowly with stirring. The solution was applied to a reversed-phase chromatography column (lenght 100 mm, diameter 14 mm; Merck Lichroprep RP-18, 15-25 u). Elution was started with 25 mL of methanol/water containing 0.3% acetic acid (10 : 90), then a linear gradient to pure methanol over a period of 75 mL was applied followed by 50 mL of pure methanol. Fraktions of 5 mL each were sampled. The solvent was evaporated to give 3.4 g of the tile compound. MS: 357

Workup

  1. washElution
  2. waita linear gradient to pure methanol over a period of 75 mL was applied followed by 50 mL of pure methanol
  3. aliquotFraktions of 5 mL each were sampled
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-3acbb0ca607745cc8c798bad7f4d03f4
Source dataset
uspto-grants-2001_02
Patent number
US06194409B1

Reaction notes

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