Diisopropylethylamine → 1,1-Dimethylethyl 4-{[3-({[(3-bromo-4-fluorophenyl)methyl]amino}carbonyl)phenyl]methyl)-1-piperidinecarboxylate

HRID 2080336Notes

Reaction equation

HRID 2080336 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][NH2:10])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:11][C:12]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][C:25]2[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=2)[C:28](O)=[O:29])[CH2:20][CH2:19]1)=[O:17])([CH3:14])[CH3:13].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][NH:10][C:28]([C:27]2[CH:26]=[C:25]([CH2:24][CH:21]3[CH2:22][CH2:23][N:18]([C:16]([O:15][C:12]([CH3:14])([CH3:13])[CH3:11])=[O:17])[CH2:19][CH2:20]3)[CH:33]=[CH:32][CH:31]=2)=[O:29])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724902(3-Bromo-4-fluorophenyl)methanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 450739593-((1-(tert-Butoxycarbonyl)piperidin-4-yl)methyl)benzoic acid

Product 1

HCID 577367091,1-Dimethylethyl 4-{[3-({[(3-bromo-4-fluorophenyl)methyl]amino}carbonyl)phenyl]methyl)-1-piperidinecarboxylateYield 94.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [(3-bromo-4-fluorophenyl)methyl]amine (0.802 g, 3.33 mmol) in DMF (12.0 mL) was added 3-[(1-{[(1,1-dimethylethyl)oxy]carbonyl}-4-piperidinyl)methyl]benzoic acid (1.060 g, 3.32 mmol), HATU (1.389 g, 3.65 mmol), and diisopropylethylamine (2.9 mL, 16.6 mmol). The reaction was allowed to stir at room temperature overnight. The reaction was diluted with EtOAc (300 mL), washed with 1N HCl (2×75 mL), then saturated NaHCO3 (3×75 mL), then brine (2×75 mL). The organic layer was dried over MgSO4, filtered, and concentrated under vacuum to give the desired product (1.58 g, 94.2%). EI-MS m/z 506(M−H)+.

Workup

  1. washwashed with 1N HCl (2×75 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4d38048d979c438fa15f22845b5c0412
Source dataset
uspto-grants-2011_04
Patent number
US07932247B2

Reaction notes

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