Hydrochloric Acid → HCID 67269365, compound

HRID 600220Notes

Reaction equation

HRID 600220 reaction equation
C(O[C:6](=[O:22])[NH:7][C:8]1[CH:13]=[C:12]([N:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH3:21])[CH2:16][CH2:15]2)[N:11]=[CH:10][N:9]=1)(C)(C)C.[CH:23]1(C(Cl)=O)[CH2:27][CH2:26][CH2:25][CH2:24]1.CCN(CC)CC.Cl>C(Cl)Cl>[CH2:20]([N:17]1[CH2:16][CH2:15][N:14]([C:12]2[N:11]=[CH:10][N:9]=[C:8]([NH:7][C:6]([CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:22])[CH:13]=2)[CH2:19][CH2:18]1)[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 78284Cyclopentanecarbonyl chlorideHCID 67269573HCID 67269573, compound

Product 1

HCID 67269365HCID 67269365, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.6 g (7.75 mmol) 6-(4-ethyl-piperazin-1-yl)-pyrimidin-4-ylamine (intermediate 4), 2.03 g (9.3 mmol) di-tert-butyl dicarbonate and 1.17 g (11.6 mmol) NEt3 in 30 mL DCM was stirred at 50° C. in a sealed tube for 16 h. After evaporation of all volatiles the residue was purified with flash column chromatography on silica. The combined product fractions were evaporated to dryness to yield [6-(4-ethyl-piperazin-1-yl)-pyrimidin-4-yl]-carbamic acid tert-butyl ester. MS(m/e): 308.4 (MH+). A mixture of 31 mg (0.1 mmol) [6-(4-ethyl-piperazin-1-yl)-pyrimidin-4-yl]-carbamic acid tert-butyl ester, 20 mg (0.15 mmol) cyclopentanecarbonyl chloride and 30 mg (0.3 mmol) NEt3 in 2 mL DCM was shaken at room temperature for 6 h. Subsequently, 3 mL HCl (4N) was added, the mixture was shaken at 50° C. for 4 h and all volatiles removed under reduced pressure. The residue was taken up in methanol/NEt3 and subjected to preparative HPLC purification on reversed phase eluting with a gradient of acetonitrile/water (0.05% triethylamine). The combined product fractions were evaporated to dryness to yield 20 mg (66%) of the title compound as white solid. MS (m/e): 344.1 (MH+).

Workup

  1. stirringthe mixture was shaken at 50° C. for 4 h
  2. customall volatiles removed under reduced pressure
  3. customsubjected to preparative HPLC purification on reversed phase
  4. washeluting with a gradient of acetonitrile/water (0.05% triethylamine)
  5. customThe combined product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-7cc63225a2084748bb0c67393da11637
Source dataset
uspto-grants-2011_03
Patent number
US07902184B2

Reaction notes

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