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1-Hydroxybenzotriazole → HCID 69371119, compound

HRID 431061
Notes
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Reaction equation

HRID 431061 reaction equation
[C:1]([C:4]1[C:9]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([Cl:20])[CH:13]=2)=[N:8][C:7]([N:21]2[CH2:25][CH2:24][CH2:23][C@H:22]2[CH2:26][OH:27])=[CH:6][N:5]=1)(O)=[O:2].[NH2:28][CH2:29][CH:30]1[O:35][CH2:34][CH2:33][N:32]([CH3:36])[CH2:31]1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O>[CH3:36][N:32]1[CH2:33][CH2:34][O:35][CH:30]([CH2:29][NH:28][C:1]([C:4]2[C:9]([NH:10][CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([Cl:20])[CH:13]=3)=[N:8][C:7]([N:21]3[CH2:25][CH2:24][CH2:23][C@H:22]3[CH2:26][OH:27])=[CH:6][N:5]=2)=[O:2])[CH2:31]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3922133(4-Methylmorpholin-2-yl)methanamineHCID 69370969HCID 69370969, compound

Product 1

HCID 69371119HCID 69371119, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of (S)-2-carboxy-3-(3-chloro-4-methoxybenzylamino)-5-(2-hydroxymethyl-1-pyrrolidinyl)pyrazine (80 mg) obtained in Example 22 (5), 2-aminomethyl-4-methylmorpholine (31.9 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (43 mg), 1-hydroxybenzotriazole (30.3 mg) in N,N-dimethylformamide (3 ml) is stirred at room temperature for 18 hours. To the reaction mixture is poured water, and the mixture is extracted with ethyl acetate. The extract is washed with water, a saturated aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel flash column chromatography (solvent; ethyl acetate) to give (S)-2-[N-(4-methyl-2-morpholinyl)methylcarbamoyl]-3-(3-chloro-4-methoxybenzylamino)-5-(2-hydroxymethyl-1-pyrrolidinyl)pyrazine (80.5 mg), MS (m/z): 505 (MH+), IR (Nujol): 3295, 1635 cm−1.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe extract is washed with water
  3. dry with materiala saturated aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel flash column chromatography (solvent; ethyl acetate)

Sources & evidence

ORD record
ord-e9fe27d86414498f913fc2ef6e90e9a7
Source dataset
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06656935B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes