Diisopropylethylamine → HCID 66685995, compound

HRID 1697301Notes

Reaction equation

HRID 1697301 reaction equation
Br[C:2]1[N:3]=[C:4]([N:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[CH:22]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:21]2)[C:5](=[O:19])[N:6]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=2[CH3:18])[C:11](OC)=[O:12])[CH:7]=1.C([O-])=O.[NH4+].C([N:46](CC)[CH:47]([CH3:49])[CH3:48])(C)C>[Pd].C(O)C>[CH:47]1([NH:46][C:11](=[O:12])[C:10]2[CH:15]=[CH:16][C:17]([CH3:18])=[C:8]([N:6]3[CH:7]=[CH:2][N:3]=[C:4]([N:20]4[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]5[CH2:29][CH2:30][CH2:31][CH2:32]5)[CH:22]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[CH2:21]4)[C:5]3=[O:19])[CH:9]=2)[CH2:49][CH2:48]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2723923Ammonium formateHCID 86669858HCID 86669858, compound

Product 1

HCID 66685995HCID 66685995, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-[5-bromo-2-oxo-3-[3-phenyl-4-[2-(1-pyrrolidinyl)ethyl]-1-piperazinyl]-1(2H)-pyrazinyl]-4-methyl-benzoic acid, methyl ester (50 mg), ammonium formate (322 mg), palladium 10% on carbon (22 mg), N,N-diisopropylethylamine (0.1 mL) and ethanol (2.5 mL) was heated under an atmosphere of nitrogen within a microwave for 30 min. at 70° C. The mixture was filtered and concentrated. Cyclopropylamine (0.3 mL) and water (0.5 mL) were added and the mixture was heated under atmosphere of nitrogen within a microwave for 5 h at 100° C. and concentrated in vacuo. Purification by preparative HPLC (Gemini column, 0.1% TFA:acetonitrile eluent) gave the title compound (30 mg).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. additionCyclopropylamine (0.3 mL) and water (0.5 mL) were added
  4. temperaturethe mixture was heated under atmosphere of nitrogen within a microwave for 5 h at 100° C.
  5. concentrationconcentrated in vacuo
  6. customPurification by preparative HPLC (Gemini column, 0.1% TFA:acetonitrile eluent)

Sources & evidence

ORD record
ord-67587939fc3e413992f236b8f437b246
Source dataset
uspto-grants-2012_04
Patent number
US08163905B2

Reaction notes

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