2-Dimethylaminopyridine → HCID 86760814, compound

HRID 1725756Notes

Reaction equation

HRID 1725756 reaction equation
[CH2:1]=[C:2]1[CH2:6][CH2:5][C:4]([CH:10]([CH3:12])[CH3:11])([C:7]([OH:9])=O)[CH2:3]1.Cl.[F:14][C:15]([F:29])([F:28])[C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:19]N.C[N:31](C1C=CC=CN=1)C.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>ClCCl>[F:14][C:15]([F:28])([F:29])[C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([C:24]([F:27])([F:25])[F:26])[CH:23]=1)[CH2:19][CH:3]1[C:2](=[CH2:1])[CH2:6][CH2:5][C:4]1([CH:10]([CH3:12])[CH3:11])[C:7]([NH2:31])=[O:9]

Participants

7

Reactant 5

HCID 218852-DimethylaminopyridineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 186143561-[3,5-Bis(trifluoromethyl)phenyl]methanamine--hydrogen chloride (1/1)HCID 18614386HCID 18614386, compound

Product 1

HCID 86760814HCID 86760814, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The solution of 3-methylene-1-isopropylcyclopentanecarboxylic acid from the previous step (1.25 g, 7.44 mmol) 3,5-bis(trifluoromethyl)benzylamine hydrochloride (2.08 g, 7.44 mmol), dimethylaminopyridine (111.0 mg, 0.91 mmol) and diisopropylethylamine (1.29 mL, 7.44 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC, 2.85 g, 14.9 mmol) in dichloromethane (50 mL) was stirred at room temperature for 24 hrs. The reaction mixture was diluted with dichloromethane (100 mL) and washed with water (3×50 mL), brine (1×50 mL), dried (anhydrous sodium sulfate) and the solvent was evaporated under reduced pressure. The crude product was purified via mplc (Lobar Fertigsaule, LiChroprep, 40-63 μm, ethyl acetate/hexanes (1:4)) yielding 910 mg (31%) of pure product. 1H NMR (500 MHz, CDCl3): 7.76 (s, 1H1), 7.70 (s, 2H), 6.20 (bs, 1H), 4.95 (bs, 1H), 4.88 (bs, 1H), 4.65 (dd, J=15.70, 6.40 Hz, 1H), 4.50 (dd, J=15.50, 5.70 Hz, 1H), 2.68 (bd, J=16.20 Hz, 1H), 2.50 to 2.10 (bm, 4H), 1.96 (h, J=6.9 Hz, 1H), 1.74 (m, 1H), 0.87 (d, J=6.9 Hz, 3H), 0.85 (d, J=7.3 Hz, 31).

Workup

  1. washwashed with water (3×50 mL), brine (1×50 mL)
  2. dry with materialdried (anhydrous sodium sulfate)
  3. customthe solvent was evaporated under reduced pressure
  4. customThe crude product was purified via mplc (Lobar Fertigsaule, LiChroprep, 40-63 μm, ethyl acetate/hexanes (1:4))

Sources & evidence

ORD record
ord-ce8744b770c043559c03e95e708e2cfe
Source dataset
uspto-grants-2009_02
Patent number
US07491737B2

Reaction notes

Loading…