Ethylenediamine → HCID 66853527, compound

HRID 1406413Notes

Reaction equation

HRID 1406413 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][N:18]3[CH2:23][CH2:22][CH:21]([F:24])[CH2:20][CH2:19]3)=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:25]1[C:26](=[O:55])[N:27](COCC[Si](C)(C)C)[CH:28]=[C:29]([NH:31][C:32]([C:34]2[CH:35]=[N:36][N:37]([CH2:39][C:40]3[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=3)[CH:38]=2)=[O:33])[CH:30]=1)=O)(C)(C)C.C(OC(C1(C2C(=O)N(COCC[Si](C)(C)C)C=C(NC(C3C=NN(CC4C=CC(C)=CC=4)C=3)=O)C=2)C=C2C(C=CC(CN3CCC(F)CC3)=C2)=N1)=O)(C)(C)C.NCCN.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(OCC)(=O)C.O1CCCC1>[F:24][CH:21]1[CH2:22][CH2:23][N:18]([CH2:17][C:13]2[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=2)[NH:8][C:9]([C:25]2[C:26](=[O:55])[NH:27][CH:28]=[C:29]([NH:31][C:32]([C:34]4[CH:35]=[N:36][N:37]([CH2:39][C:40]5[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=5)[CH:38]=4)=[O:33])[CH:30]=2)=[CH:10]3)[CH2:19][CH2:20]1

Participants

7

Reactant 4

HCID 3301EthylenediamineHCID 2724141Tetrabutylammonium FluorideHCID 58117377HCID 58117377, compoundHCID 66853600HCID 66853600, compound

Product 1

HCID 66853527HCID 66853527, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A 2-5 mL microwave vial was charged with intermediate (8g), 5-(4-fluoro-piperidin-1-ylmethyl)-2-[5-{[1-(4-methyl-benzyl)-1H-pyrazole-4-carbonyl]amino}-2-oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,2-dihydro-pyridin-3-yl]-indolecarboxylic acid tert-butyl ester (96 mg, 0.125 mmol), tetrahydrofuran (3 mL), 1,2-diaminoethane (38 mg, 42 ul, 0.63 mmol) and finally tetrabutylammonium fluoride solution 1.0M in tetrahydrofuran (0.63 mL, 0.63 mmol). The vial was heated under microwave irradiation at 120° C. for 20 mins. After cooling, the reaction mixture was diluted with ethyl acetate (20 mL) and washed with water (4×20 mL) and brine (4×20 mL). The organics were dried (Na2SO4) and concentrated in vacuo. The resultant yellow solid was purified via trituration using acetonitrile, to afford the title compound as a yellow solid, 42 mg, 63%.

Workup

  1. temperatureAfter cooling
  2. washwashed with water (4×20 mL) and brine (4×20 mL)
  3. dry with materialThe organics were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe resultant yellow solid was purified via trituration

Sources & evidence

ORD record
ord-098139abcf58443081f92bd419dcf29b
Source dataset
uspto-grants-2014_12
Patent number
US08916591B2

Reaction notes

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