Cyclopropylamine → HCID 178517931, compound

HRID 1296804Notes

Reaction equation

HRID 1296804 reaction equation
CS[C:3]1[S:4][C:5](=[CH:9][C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)[C:6](=[O:8])[N:7]=1.[CH:19]1([NH2:22])[CH2:21][CH2:20]1.C(N(C(C)C)CC)(C)C>C(#N)C>[CH:19]1([NH:22][C:3]2[S:4]/[C:5](=[CH:9]\[C:10]3[C:18]4[C:13](=[N:14][CH:15]=[CH:16][CH:17]=4)[NH:12][CH:11]=3)/[C:6](=[O:8])[N:7]=2)[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 178503545HCID 178503545, compound

Product 1

HCID 178517931HCID 178517931, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

The suspension of 2-methylsulfanyl-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylene)-thiazol-4-one (55 mg, 02 mmol, example 14a), cyclopropylamine (23 mg, 0.4 mmol) and diisopropylethylamine (DIEA) (70 uL, 0.4 mmol) in acetonitrile (1.0 mL) was stirred under at 80° C. for 12 h. After cooling to room temperature, the solid was collected by filtration, washed with a little bit of acetonitrile and dried. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 0%-10% methanol in methylene chloride in 30 min) afforded 2-cyclopropylamino-5-[1-(1H-pyrrolo[2,3-b]pyridin-3-yl)-meth-(Z)-ylidene]-thiazol-4-one (40 mg, 71%) as a light yellow solid. LC-MS m/e 285 (MH+).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe solid was collected by filtration
  3. washwashed with a little bit of acetonitrile
  4. customdried

Sources & evidence

ORD record
ord-9e580b9a1fca4c849c0cc3b691cdd35f
Source dataset
uspto-grants-2007_07
Patent number
US07247727B2

Reaction notes

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