Triethylamine → HCID 178482132, compound

HRID 504161Notes

Reaction equation

HRID 504161 reaction equation
C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[F:41][C:42]([F:62])([F:61])[C:43]1[CH:44]=[C:45]([S:49]([N:52]2[CH2:57][CH2:56][CH2:55][CH2:54][C@H:53]2[C:58]([OH:60])=O)(=[O:51])=[O:50])[CH:46]=[CH:47][CH:48]=1.[NH2:63][C@@H:64]([CH2:75][C:76]1[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1)/[CH:65]=[N:66]/[C:67]1[C:68]([NH:73][CH3:74])=[CH:69][CH:70]=[CH:71][CH:72]=1>C(Cl)Cl>[CH2:75]([C@H:64]([NH:63][C:58]([C@@H:53]1[CH2:54][CH2:55][CH2:56][CH2:57][N:52]1[S:49]([C:45]1[CH:46]=[CH:47][CH:48]=[C:43]([C:42]([F:41])([F:61])[F:62])[CH:44]=1)(=[O:50])=[O:51])=[O:60])/[CH:65]=[N:66]/[C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][C:68]=1[NH:73][CH3:74])[C:76]1[CH:77]=[CH:78][CH:79]=[CH:80][CH:81]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 59428653HCID 59428653, compoundHCID 178482134HCID 178482134, compound

Product 1

HCID 178482132HCID 178482132, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

PyBOP (0.11 g, 0.22 mmoles) and triethylamine (0.076 mL, 0.55 mmoles) were added to a room temperature solution of (S)-1-(3-trifluoromethyl-benzenesulfonyl)-piperidine-2-carboxylic acid (0.074 g, 0.22 mmol) in CH2Cl2 (5 mL). After stirring at room temperature for 20 min, a solution of N-[(S)-2-amino-3-phenyl-prop-(E)-ylidene]-N′-methyl-benzene-1,2-diamine (0.052 g, 0.22 mmoles) in CH2Cl2 (5 mL) was added, and the resulting mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with CH2Cl2 (100 mL) and washed with saturated aqueous NaHCO3 (100 mL) and brine (100 mL). The organic layer was dried (MgSO4) and concentrated in vacuo to give a yellow oil. Purification of the residue by flash chromatography on silica gel, eluting with 10-50% EtOAc/heptane afforded 0.078 g (64%) of the title compound as a colorless powder: ES+ LC/MS m/e 557 (M+H), RT=2.92 min; 1H NMR CDCl3: δ9.99 (bd s, 1), 8.05 (s, 1), 7.94 (d, 1, J=8.0 Hz), 7.83 (d, 1, J=7.9 Hz), 7.62 (t, 1, J=7.9 Hz), 7.23-7.56 (m, 8), 7.00 (d, 1, J=7.5 Hz), 5.45 (m, 1), 4.40 (bd s, 1), 3.72 (dd, 1, J=14.5, 5.1 Hz), 3.54 (d, 1, J=14.1 Hz), 3.44 (dd, 1, J=14.5, 10.8 Hz), 2.13-2.26 (m, 2), 1.37 (m, 1), 1.22 (m, 1), 0.92-1.10 (m, 4).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 16 h
  2. washwashed with saturated aqueous NaHCO3 (100 mL) and brine (100 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give a yellow oil
  6. customPurification of the residue by flash chromatography on silica gel
  7. washeluting with 10-50% EtOAc/heptane

Sources & evidence

ORD record
ord-ecb3af95d73c4c33a1ad5122eb7660c4
Source dataset
uspto-grants-2010_08
Patent number
US07777042B2

Reaction notes

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