4-Methylmorpholine → HCID 66922363, compound

HRID 2039827Notes

Reaction equation

HRID 2039827 reaction equation
[Cl:1][C:2]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]2=[CH:6][N:7]=[C:8]([O:10][CH3:11])[CH:9]=[C:4]2[C:3]=1[C:19](O)=[O:20].[N:22]1([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C>[C:31]([O:30][C:28]([N:22]1[CH2:27][CH2:26][N:25]([C:19]([C:3]2[C:4]3[C:5](=[CH:6][N:7]=[C:8]([O:10][CH3:11])[CH:9]=3)[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:2]=2[Cl:1])=[O:20])[CH2:24][CH2:23]1)=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66922130HCID 66922130, compound

Product 1

HCID 66922363HCID 66922363, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the crude compound of step 4, tert-butyl 1-piperazinecarboxylate (565 mg, 3.03 mmol), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (581 mg, 3.03 mmol) and 1-hydroxybenzotriazole hydrate (312 mg, 2.29 mmol) in DMF (20 ml) was added NMM (911 μl, 8.27 mmol), and the reaction mixture was stirred at room temperature overnight. The mixture was quenched with water and extracted with EA. The organic layer was separated, dried over sodium sulfate, filtered and evaporated.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EA
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4c37e7dda74447eb9d09f68c537e59ea
Source dataset
uspto-grants-2013_11
Patent number
US08580813B2

Reaction notes

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