Triethylamine → HCID 86665066, compound

HRID 333350Notes

Reaction equation

HRID 333350 reaction equation
[Cl:1][C:2](=[CH2:12])[CH2:3][C:4]1([C:9]([OH:11])=O)[CH2:8][CH2:7][CH2:6][CH2:5]1.CCN=C=NCCCN(C)C.Cl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C.OC(C(F)(F)F)=O.[NH2:49][C@@H:50]([CH2:55][C:56]1[CH:61]=[CH:60][C:59]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)=[CH:58][CH:57]=1)[C:51]([NH:53][CH3:54])=[O:52]>CN(C=O)C>[C:59]1([C:62]2[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=2)[CH:60]=[CH:61][C:56]([CH2:55][C@H:50]([NH:49][C:9]([C:4]2([CH2:3][C:2]([Cl:1])=[CH2:12])[CH2:5][CH2:6][CH2:7][CH2:8]2)=[O:11])[C:51]([NH:53][CH3:54])=[O:52])=[CH:57][CH:58]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86665070HCID 86665070, compoundHCID 86665072HCID 86665072, compound

Product 1

HCID 86665066HCID 86665066, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2-chloroallyl)cyclopentanecarboxylic acid (50 mg, 0.27 mmol) in DMF (1.2 mL) was added EDC.HCl (51 mg, 0.27 mmol), HOAt (29 mg, 0.21 mmol) and triethylamine (0.04 mL, 0.27 mmol). To the mixture stirred at room temperature was added (S)-2-amino-3-(biphenyl-4-yl)-N-methylpropanamide TFA salt (45 mg, 0.18 mmol). The mixture was stirred at room temperature for 18 hours. The mixture was extracted with EtOAc, and the organic layer was washed with water (8 times), brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The obtained residue was purified by TLC preparation plates using 70% EtOAc/heptane to give (S)—N-(3-(biphenyl-4-yl)-1-(methylamino)-1-oxopropan-2-yl)-1-(2-chloroallyl)cyclopentanecarboxamide (38 mg). HPLC retention time=1.69 minutes (condition B); MS (m+1)=425.0; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.34-1.64 (m, 6H), 1.79-2.02 (m, 2H), 2.59 (d, J=5.8 Hz, 2H), 2.66 (d, J=4.9 Hz, 3H), 3.05 (d, J=7.3 Hz, 2H), 4.66 (q, J=7.5 Hz, 1H), 4.95 (s, 1H), 5.05 (s, 1H), 6.28-6.35 (m, 1H), 6.37 (d, J=7.7 Hz, 1H), 7.20 (d, J=8.2 Hz, 2H), 7.23-7.30 (m, 1H), 7.34 (t, J=7.5 Hz, 2H), 7.45 (dd, J=14.5, 7.8 Hz, 4H).

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic layer was washed with water (8 times), brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by TLC preparation plates

Sources & evidence

ORD record
ord-b5b307001b4e41e998647aa2e5585f78
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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