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Isobutyl chloroformate → 2-[(8-chlorodibenz[b,f][1,4]oxazepin-10(11H)-yl)carbonyl]-N-(4-pyridinylmethyl)benzamide, hydrochloride

HRID 37355
Notes
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Reaction equation

HRID 37355 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[O:6][C:7]3[CH:25]=[CH:24][CH:23]=[CH:22][C:8]=3[CH2:9][N:10]([C:11]([C:13]3[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=3[C:15](O)=[O:16])=[O:12])[C:4]=2[CH:3]=1.C(OC(Cl)=O)C(C)C.[NH2:36][CH2:37][C:38]1[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=1>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[O:6][C:7]3[CH:25]=[CH:24][CH:23]=[CH:22][C:8]=3[CH2:9][N:10]([C:11]([C:13]3[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=3[C:15]([NH:36][CH2:37][C:38]3[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=3)=[O:16])=[O:12])[C:4]=2[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 62365Isobutyl chloroformateHCID 773174-PyridinemethanamineHCID 157806572-[(8-chlorodibenz[b,f][1,4]oxazepin-10(11H)-yl)carbonyl]benzoic acid

Product 1

HCID 1317190132-[(8-chlorodibenz[b,f][1,4]oxazepin-10(11H)-yl)carbonyl]-N-(4-pyridinylmethyl)benzamide, hydrochloride

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a stirred solution of the title product of Example 11 (0.55 g) in CH2Cl2 (10 mL) at 0° C. was added 1-methyl morpholine (0.168 mL) and isobutylchloroformate (0.199 mL) successively. After 30 minutes, 4-(aminomethyl)pyridine (0.156 mL) was added. The mixture was allowed to warm to ambient temperature for hours. The mixture was extracted with ethyl acetate and water. The organic extract was dried over MgSO4 and concentrated. The residue was purified by chromatography over silica gel using ethyl acetate as eluant to give the free base of the title compound as a white solid. The hydrochloride salt of the free base was made in the manner described in Example 3 to give the title compound.

Workup

  1. extractionThe mixture was extracted with ethyl acetate and water
  2. extractionThe organic extract
  3. dry with materialwas dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-5cbc34ffa9f54a88b61082ab7fa8a56e
Source dataset
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05420270

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes