Triethylamine → HCID 12074891, compound

HRID 457746Notes

Reaction equation

HRID 457746 reaction equation
C(N(CC)CC)C.FC(F)(F)C(O)=O.[NH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][C:26]=2[NH:30][C:31]([C:33]2[S:34][C:35]([Cl:38])=[CH:36][CH:37]=2)=[O:32])[C:21]1=[O:39].Cl.[C:41](Cl)(=[O:48])[C:42]1[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=1>CN(C)C1C=CN=CC=1.C1COCC1.ClCCl>[Cl:38][C:35]1[S:34][C:33]([C:31]([NH:30][C:26]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:27]=2[C:28](=[O:29])[N:20]([CH2:19][CH2:18][CH2:17][CH2:16][NH:15][C:41](=[O:48])[C:42]2[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=2)[C:21]3=[O:39])=[O:32])=[CH:37][CH:36]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 18440724HCID 18440724, compound

Product 1

HCID 12074891HCID 12074891, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

25 mg (0.24 mmol) of triethylamine and a catalytic amount of 4-dimethylaminopyridine are added to 40 mg (0.08 mmol) of N-[2-(4-aminobutyl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]-5-chloro-2-thiophenecarboxamide trifluoroacetate in 2 ml of THF. At 0° C., 17.4 mg (0.10 mmol) of isonicotinoyl chloride hydrochloride are then added. The reaction mixture is warmed to RT, stirred at RT for 3 h and then heated at reflux for 20 h. After cooling to RT, the reaction mixture is diluted with dichloromethane and washed with aqu. sat. NaHCO3 solution. The organic phase is dried over MgSO4, filtered and concentrated. The crude product is chromatographed on silica gel (CH2Cl2/EtOH=50/1). This gives 18.5 mg (47% of theory) of the desired product.

Workup

  1. temperatureheated
  2. temperatureat reflux for 20 h
  3. temperatureAfter cooling to RT
  4. washwashed with aqu
  5. dry with materialThe organic phase is dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is chromatographed on silica gel (CH2Cl2/EtOH=50/1)

Sources & evidence

ORD record
ord-154c9afbdacf4aae83d25e09cb4b4dff
Source dataset
uspto-grants-2007_03
Patent number
US07189738B2

Reaction notes

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