1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 23076606, compound

HRID 2221953Notes

Reaction equation

HRID 2221953 reaction equation
Cl.[CH3:2]OCN.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:22]=[CH:23][C:24]=1[O:25][CH2:26][C:27]1[N:28]=[C:29]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:30][C:31]=1[CH3:32])[CH2:11][O:12][C:13]1[C:17]([C:18]([OH:20])=O)=[CH:16][N:15]([CH3:21])[N:14]=1.O.[OH:40][N:41]1[C:45]2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O.CN(C)C=O.C(N(CC)CC)C>[CH3:2][O:40][N:41]([CH3:45])[C:18]([C:17]1[C:13]([O:12][CH2:11][C:10]2[CH:22]=[CH:23][C:24]([O:25][CH2:26][C:27]3[N:28]=[C:29]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[O:30][C:31]=3[CH3:32])=[C:8]([O:7][CH3:6])[CH:9]=2)=[N:14][N:15]([CH3:21])[CH:16]=1)=[O:20]

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 21959107Methoxymethanamine hydrochlorideHCID 692152243-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-methyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 23076606HCID 23076606, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of methoxymethylamine hydrochloride (0.85 g), triethylamine (1.3 mL) and N,N-dimethylformamide (20 mL) was stirred at room temperature for 30 min. To the reaction mixture were added 3-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-methyl-1H-pyrazole-4-carboxylic acid (3.45 g), 1-hydroxy-1H-1,2,3-benzotriazole monohydrate (1.22 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.60 g), and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with dilute hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated to give N-methoxy-N-methyl-3-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-methyl-1H-pyrazole-4-carboxamide (3.63 g, yield 96%) as colorless crystals. The crystals were recrystallized from acetone-hexane. melting point: 138-139° C.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed successively with dilute hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5b4f49ad74714244a183a1679457dd56
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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