4-Methylmorpholine → HCID 66705633, compound

HRID 425416Notes

Reaction equation

HRID 425416 reaction equation
CN1CCOCC1.[Cl-].[C:9]([C:12]1([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][NH+:26]=3)=[CH:21][CH:20]=2)[CH2:16][CH2:15][C:14](=[O:17])[NH:13]1)([OH:11])=O.[Cl-].[Na+].[NH2:34][CH2:35][CH:36]([OH:43])[CH2:37][C:38]([CH3:42])([CH3:41])[CH2:39][CH3:40].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C(Cl)Cl.C(OCC)(=O)C>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:22]2[CH:21]=[CH:20][C:19]([CH2:18][C:12]3([C:9]([NH:34][CH2:35][CH:36]([OH:43])[CH2:37][C:38]([CH3:42])([CH3:41])[CH2:39][CH3:40])=[O:11])[CH2:16][CH2:15][C:14](=[O:17])[NH:13]3)=[CH:24][CH:23]=2)=[N:26][CH:27]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 55289824HCID 55289824, compoundHCID 66705715HCID 66705715, compound

Product 1

HCID 66705633HCID 66705633, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-methylmorpholine (0.37 mL, 3.32 mmol) was added to an ambient temperature solution of 2-{4-[(2-carboxy-5-oxopyrrolidin-2-yl)methyl]phenyl}-5-fluoropyridinium chloride/sodium chloride (1:3) (388 mg, 0.74 mmol), 1-amino-4,4-dimethylhexan-2-ol (214 mg, 1.48 mmol), 1-[3-(dimethylamino) propyl]-3-ethylcarbodiimide hydrochloride (170 mg, 0.89 mmol) and 1-hydroxybenzotriazole (136 mg, 0.89 mmol) in methylene chloride (5 mL). After stirring at ambient temperature overnight, the reaction mixture was poured into ethyl acetate and washed successively with saturated aqueous sodium bicarbonate and brine, dried (sodium sulfate) and concentrated in vacuo to afford 2-[4-(5-fluoropyridin-2-yl)benzyl]-N-(2-hydroxy-4,4-dimethylhexyl)-5-oxopyrrolidine-2-carboxamide which was used in the subsequent step without further purification.

Workup

  1. washwashed successively with saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-12d6574c451d4f7f9bfb24bc54d5247c
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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