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1-Hydroxybenzotriazole → HCID 68797990, compound

HRID 1375386
Notes
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Reaction equation

HRID 1375386 reaction equation
[Cl:1][C:2]1[CH:30]=[C:29]([N:31]2[CH:35]=[CH:34][C:33]([CH3:36])=[N:32]2)[CH:28]=[CH:27][C:3]=1[C:4]([N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2/[C:10](=[CH:17]/[C:18]([NH:20][CH2:21][C:22](O)=[O:23])=[O:19])/[C:9]([F:26])([F:25])[CH2:8][CH2:7]1)=[O:5].C1C=CC2N(O)N=[N:43][C:41]=2C=1.CCN=C=NCCCN(C)C.Cl.CN.C1COCC1.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:1][C:2]1[CH:30]=[C:29]([N:31]2[CH:35]=[CH:34][C:33]([CH3:36])=[N:32]2)[CH:28]=[CH:27][C:3]=1[C:4]([N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2/[C:10](=[CH:17]/[C:18]([NH:20][CH2:21][C:22]([NH:43][CH3:41])=[O:23])=[O:19])/[C:9]([F:26])([F:25])[CH2:8][CH2:7]1)=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 44520870HCID 44520870, compoundHCID 66615946Methylamine tetrahydrofuran

Product 1

HCID 68797990
HCID 68797990, compound
Yield 19.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 258 mg of the compound of Example 10, 71 mg of HOBt and 101 mg of EDCI.HCl in 5 ml of THF, and 0.5 ml of 2.0 M methylamine-THF solution were added, and the mixture was stirred at room temperature overnight. The reaction solution was mixed with saturated NaHCO3 aq. and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate. The crude product obtained by evaporation of the solvent was purified by silica gel column chromatography (chloroform-MeOH (30:1)). The residue obtained by concentration under reduced pressure was crystallized from a 2-propanol-hexane solvent mixture to obtain 51 mg of (2Z)-2-{1-[2-chloro-4-(3-methyl-1H-pyrazol-1-yl)benzoyl]-4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepin-5-ylidene}-N-[2-(methylamino)-2-oxoethyl]acetamide.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe crude product obtained by evaporation of the solvent
  4. customwas purified by silica gel column chromatography (chloroform-MeOH (30:1))
  5. customThe residue obtained by concentration under reduced pressure
  6. customwas crystallized from a 2-propanol-hexane solvent mixture

Sources & evidence

ORD record
ord-6dccc9f7f5be40ab8c00b2c509096445
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07169772B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes