Benzoyl chloride → HCID 23624277, compound

HRID 1684892Notes

Reaction equation

HRID 1684892 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]([N:10]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12][CH2:11]2)=[N:8][CH:9]=1)([O-])=O.N12CCC(CC1)N(C1N=CC(N)=CN=1)CC2.[C:35]([Cl:43])(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>[Pd].C(O)C>[ClH:43].[N:13]12[CH2:18][CH2:17][CH:16]([CH2:15][CH2:14]1)[N:10]([C:7]1[N:6]=[CH:5][C:4]([NH:1][C:35](=[O:42])[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:9][N:8]=1)[CH2:11][CH2:12]2

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 66630811HCID 66630811, compoundHCID 66631372HCID 66631372, compound

Product 1

HCID 23624277HCID 23624277, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(5-nitro-pyrimidin-2-yl)-1,4-diaza-bicyclo[3.2.2]nonane (0.86 g, 2.9 mmol), palladium (0.25 g, 10% on activated carbon) and ethanol (50 ml) was stirred under hydrogen for 10 min (200 ml of hydrogen consumed). The rection-mixture of 2-(1,4-diaza-bicyclo[3.2.2]non-4-yl)-pyrimidin-5-ylamine was filtered through celite and was washed with ethanol (50 ml). The ethanolic solution of 2-(1,4-diaza-bicyclo[3.2.2]non-4-yl)-pyrimidin-5-ylamine was mixed with benzoylchloride 0.41 g, 2.90 mmol) and was stirred for 15 h at room-temperature. The title product precipitated as hydrochloric acid salt by addition of hydrochloric acid in ethanol. Yield 0.38 g (36%). LC-ESI-HRMS of [M+H]+ shows 324.1817 Da. Calc. 324.182435 Da, dev. −2.3 ppm.

Workup

  1. custom(200 ml of hydrogen consumed)
  2. additionThe rection-mixture of 2-(1,4-diaza-bicyclo[3.2.2]non-4-yl)-pyrimidin-5-ylamine
  3. filtrationwas filtered through celite
  4. washwas washed with ethanol (50 ml)
  5. stirringwas stirred for 15 h at room-temperature
  6. customThe title product precipitated as hydrochloric acid salt by addition of hydrochloric acid in ethanol

Sources & evidence

ORD record
ord-0dd2b86b0ce34417bf884764ef876a76
Source dataset
uspto-grants-2012_04
Patent number
US08148365B2

Reaction notes

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