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2,6-Dimethylbenzoic acid → 2,6-Dimethyl-N-[[1-(methylamino)cyclopentyl](phenyl)methyl]benzamide

HRID 20844
Notes
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Reaction equation

HRID 20844 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=O.[NH2:12][CH:13]([C:20]1(CN)[CH2:24][CH2:23][CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:27][N:28](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCN(C(C)C)C(C)C>[CH3:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:2]([CH3:1])[C:3]=1[C:4]([NH:12][CH:13]([C:20]1([NH:28][CH3:27])[CH2:21][CH2:22][CH2:23][CH2:24]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 124392,6-Dimethylbenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57444874{[Amino(phenyl)methyl]cyclopentyl}methylamine

Product 1

HCID 115228862,6-Dimethyl-N-[[1-(methylamino)cyclopentyl](phenyl)methyl]benzamideYield 76%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of 2,6-dimethylbenzoic acid (0.100 g; 0.668 mmol) in DMF (5 ml) and DIPEA (0.12 ml) was added {[amino(phenyl)methyl]cyclopentyl}methylamine D31 enantiomer 2 (0.124 g; 0.608 mmol) and HATU (0.254 g; 0.668 mmol). The resulting mixture was allowed to stir at room temperature for 3 days and then the DMF was evaporated off under reduced pressure. Residual material was partitioned between ethyl acetate and water, washed with water and the organic layer was dried (Na2SO4) and evaporated. The residual material was dissolved in DCM (2 ml) and loaded onto an SCX cartridge. Washing with DCM, then methanol followed by elution with 1 M ammonia in methanol afforded the title product (155 mg; 76%). 1H NMR (CDCl3) δ: 1.3-1.8 (9H, m), 2.21 (3H, s), 2.28 (6H, s), 5.07 (1H, m), 7.0 (2H, m), 7.1-7.4 (7H, m). Mass Spectrum (Electrospray LC/MS). Found 337 (MH+). C22H28N2O requires 336. Ret. time: 1.86 min.

Workup

  1. customthe DMF was evaporated off under reduced pressure
  2. customResidual material was partitioned between ethyl acetate and water
  3. washwashed with water
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. customevaporated
  6. dissolutionThe residual material was dissolved in DCM (2 ml)
  7. washWashing with DCM
  8. washmethanol followed by elution with 1 M ammonia in methanol

Sources & evidence

ORD record
ord-4d7b6c3ca3c241229878f9f0254ed117
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07745642B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes