Hydrochloric Acid → HCID 960976, compound

HRID 555389Notes

Reaction equation

HRID 555389 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH2:32][CH:33]1[CH:40]2[CH2:41][CH:36]3[CH2:37][CH:38]([CH2:42][CH:34]1[CH2:35]3)[CH2:39]2.Cl.CCN(C(C)C)C(C)C>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:32][CH:33]2[CH:34]3[CH2:42][CH:38]4[CH2:37][CH:36]([CH2:41][CH:40]2[CH2:39]4)[CH2:35]3)=[O:8])=[CH:9][CH:10]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 99734-Fluorobenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 253322-AminoadamantaneHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 960976HCID 960976, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-fluorobenzoic acid (15.0 g, 0.11 mol) in DMF (400 mL) was added HOBt (24.59 g, 0.16 mol) and EDAC (20.53 g, 0.11 mol). The resulting mixture was stirred for 1 hr at room temperature at which time a solution of 2-amino-adamantane.HCl (20.1 g, 0.11 mol) and DIPEA (20.52 mL) in DMF (100 mL) was added dropwise. The mixture was stirred at room temperature for 16 hrs and the volatiles evaporated in vacuo. The residue was dissolved in AcOEt and washed with aq. NaHCO3, brine, dried (MgSO4), filtered and the solvent evaporated in vacuo affording 28.66 g, (98%) of 4-fluoro-N-adamantan-2-yl-benzamide as a solid.

Workup

  1. customthe volatiles evaporated in vacuo
  2. dissolutionThe residue was dissolved in AcOEt
  3. washwashed with aq. NaHCO3, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-c3719ffbfb024944911993f5e9f6ec71
Source dataset
uspto-grants-2011_11
Patent number
US08053447B2

Reaction notes

Loading…