4-Methylmorpholine → HCID 118251619, compound

HRID 2203179Notes

Reaction equation

HRID 2203179 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11][C:12]([OH:14])=O)[CH:10]=1)[N:7]([CH2:15][CH:16]([CH3:18])[CH3:17])[N:6]=[CH:5]2.Cl.Cl.[NH2:21][CH2:22][C:23]1[CH:28]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[CH:26]=[CH:25][N:24]=1.Cl.CN(C)CCCN=C=NCC.CN1CCOCC1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11][C:12]([NH:21][CH2:22][C:23]3[CH:28]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[CH:26]=[CH:25][N:24]=3)=[O:14])[CH:10]=1)[N:7]([CH2:15][CH:16]([CH3:18])[CH3:17])[N:6]=[CH:5]2

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 71756766HCID 71756766, compoundHCID 118251613HCID 118251613, compound

Product 1

HCID 118251619HCID 118251619, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of compound 58 (0.155 g, 0.58 mmoles) and methyl 2-(aminomethyl)pyridine-4-carboxylate dihydrochloride (0.139 g, 0.58 mmoles) (see WO2003070732, example 6, step 2 for preparation, which is incorporated by reference in its entirety) in dichloromethane (20 ml) was treated with N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uranium hexafluorophosphate (0.264 g, 0.69 mmoles) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.133 g, 0.69 mmoles) and N-methylmorpholine (0.255 ml, 2.32 mmoles) then stirred at ambient temperature under a nitrogen atmosphere for 18 h. The mixture was washed with water (2×20 ml) and saturated brine (20 ml) then separated and dried over sodium sulphate, filtered and evaporated to dryness. The residue was chromatographed on silica gel eluting with an ethyl acetate/isohexane gradient. This gave the title compound as a colorless oil (0.184 g 76%).

Workup

  1. washThe mixture was washed with water (2×20 ml) and saturated brine (20 ml)
  2. customthen separated
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was chromatographed on silica gel eluting with an ethyl acetate/isohexane gradient

Sources & evidence

ORD record
ord-09f1c884302a4e7a888c9492c1c73b5c
Source dataset
uspto-grants-2016_06
Patent number
US09365569B2

Reaction notes

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