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Methylamine → 1,1-Dimethylethyl 7-({5-[(methylamino)carbonyl]-2-pyrazinyl}oxy)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

HRID 645797
Notes
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Reaction equation

HRID 645797 reaction equation
[C:1](N1C=CN=C1)([N:3]1C=CN=C1)=O.[CH3:13][C:14]([O:17][C:18]([N:20]1[CH2:26][CH2:25][C:24]2[CH:27]=[CH:28][C:29]([O:31][C:32]3[N:33]=[CH:34][C:35]([C:38]([OH:40])=O)=[N:36][CH:37]=3)=[CH:30][C:23]=2[CH2:22][CH2:21]1)=[O:19])([CH3:16])[CH3:15].CN>ClCCl>[CH3:1][NH:3][C:38]([C:35]1[N:36]=[CH:37][C:32]([O:31][C:29]2[CH:28]=[CH:27][C:24]3[CH2:25][CH2:26][N:20]([C:18]([O:17][C:14]([CH3:13])([CH3:16])[CH3:15])=[O:19])[CH2:21][CH2:22][C:23]=3[CH:30]=2)=[N:33][CH:34]=1)=[O:40]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 574376215-[(3-{[(1,1-Dimethylethyl)oxy]carbonyl}-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-2-pyrazinecarboxylic acid

Product 1

HCID 685073281,1-Dimethylethyl 7-({5-[(methylamino)carbonyl]-2-pyrazinyl}oxy)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylateYield 66.8%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

1,1′-Carbonyldiimidazole (16.6 g, 102 mmol) was added to a solution of 5-[(3-{[(1,1-dimethylethyl)oxy]carbonyl}-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-2-pyrazinecarboxylic acid (D49, Step 2) (37.5 g, 97 mmol) in dry dichloromethane (400 ml) and the resulting mixture was stirred at room temperature for 18 hours. Methylamine (2M solution in tetrahydrofuran) (100 ml) was added and the mixture stirred for 2 hours. The solvent was removed in vacuo and the residue was purified by column chromatography eluting with a mixture of ethyl acetate:chloroform (1:1) to afford the title compound (25.8 g); MS (ES+) m/e 399 [M+H]+.

Workup

  1. stirringthe mixture stirred for 2 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by column chromatography
  4. washeluting with a mixture of ethyl acetate:chloroform (1:1)

Sources & evidence

ORD record
ord-aebf0d90299c486ab8c9eafd4c6bc262
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07704994B2

Reaction notes

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