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Dicyclohexylcarbodiimide → 3-cyano-N-[2-(4-fluoro-2-methylphenyl)-4-(tetrahydro-2H-pyran-2-yloxy)butyl]-5,6,7,8-tetrahydronaphthalene-1-carboxamide

HRID 749470
Notes
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Reaction equation

HRID 749470 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][CH2:12][O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH2:9][NH2:10])=[C:4]([CH3:20])[CH:3]=1.[C:21]([C:23]1[CH:24]=[C:25]([C:33](O)=[O:34])[C:26]2[CH2:27][CH2:28][CH2:29][CH2:30][C:31]=2[CH:32]=1)#[N:22].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[C:21]([C:23]1[CH:24]=[C:25]([C:33]([NH:10][CH2:9][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[CH3:20])[CH2:11][CH2:12][O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)=[O:34])[C:26]2[CH2:27][CH2:28][CH2:29][CH2:30][C:31]=2[CH:32]=1)#[N:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 224526443-Cyano-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acidHCID 68976391[2-(4-Fluoro-2-methylphenyl)-4-(tetrahydro-2H-pyran-2-yloxy)butyl]amine

Product 1

HCID 689801273-cyano-N-[2-(4-fluoro-2-methylphenyl)-4-(tetrahydro-2H-pyran-2-yloxy)butyl]-5,6,7,8-tetrahydronaphthalene-1-carboxamideYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

[2-(4-Fluoro-2-methylphenyl)-4-(tetrahydro-2H-pyran-2-yloxy)butyl]amine (0.40 g, 1.4 mmol), 3-cyano-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid (see WO 00/34243; 0.32 g, 1.6 mmol) and DCC (0.35 g, 1.7 mmol) were mixed with CH2Cl2 (5 mL). The mixture was stirred at room temperature overnight and then filtrated and the solvent was evaporated. The product was purified by chromatography on silica gel using methanol and CH2Cl2 (0%-2% methanol). There was obtained 600 mg (91%) of 3-cyano-N-[2-(4-fluoro-2-methylphenyl)-4-(tetrahydro-2H-pyran-2-yloxy)butyl]-5,6,7,8-tetrahydronaphthalene-1-carboxamide as a foam. 1H NMR (500 MHz, CDCl3): 1.0-1.9 (m, 9H), 2.0-2.1 (m, 1H), 2.4 (d, 3H), 2.6-2.8 (m, 4H), 3.2-3.8 (m, 7H), 4.4-4.5 (d, 1H), 6.0-6.2 (m, 1H), 6.9 (m, 2H), 7.1-7.3 (m, 2H), 7.4 (s, 1H). LCMS: m/z 463 (M−1)−.

Workup

  1. filtrationfiltrated
  2. customthe solvent was evaporated
  3. customThe product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-20a99faf95b84b99b303269d55ab182d
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07402581B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes