Hydrochloric Acid → HCID 131720060, compound

HRID 362737Notes

Reaction equation

HRID 362737 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:28][CH2:29]OS(C)(=O)=O)[O:14][CH2:13][CH2:12][N:11]([C:15](=[O:27])[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH:24]([CH3:26])[CH3:25])[CH:18]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[N:35]1([CH:41]2[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.O.[ClH:48]>CN(C=O)C.CCOCC>[OH2:14].[ClH:48].[ClH:48].[F:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:28][CH2:29][N:44]3[CH2:45][CH2:46][CH:41]([N:35]4[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]4)[CH2:42][CH2:43]3)[O:14][CH2:13][CH2:12][N:11]([C:15](=[O:27])[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH:24]([CH3:26])[CH3:25])[CH:18]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[F:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:28][CH2:29][N:44]3[CH2:45][CH2:46][CH:41]([N:35]4[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]4)[CH2:42][CH2:43]3)[O:14][CH2:13][CH2:12][N:11]([C:15](=[O:27])[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH:24]([CH3:26])[CH3:25])[CH:18]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[ClH:48].[ClH:48]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 786071,4'-BipiperidineHCID 21200564HCID 21200564, compound

Product 1

HCID 131720060HCID 131720060, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1.3 g of the compound obtained in step C of EXAMPLE 71 and 1.1 g of 4-(piperid-1-yl)-piperidine in 4 ml of DMF is heated at 70° C. for 4 hours. After cooling to RT, the reaction mixture is poured into iced water and extracted with AcOEt, the organic phase is washed with 1N NaOH solution and with saturated NaCl solution and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica H using DCM and then a DCM/MeOH mixture (90/10; v/v) as the eluent. The product obtained is taken up with a saturated solution of hydrochloric acid in ether and the precipitate formed is wrung to give 0.49 g of the expected product. M.p.=270° C. (dec.).

Workup

  1. temperatureAfter cooling to RT
  2. extractionextracted with AcOEt
  3. washthe organic phase is washed with 1N NaOH solution and with saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. customthe solvent is evaporated off under vacuum
  6. customThe residue is chromatographed on silica H
  7. customThe product obtained
  8. customthe precipitate formed

Sources & evidence

ORD record
ord-c0657193a8f840abac4629d2c5c190d9
Source dataset
uspto-grants-1999_02
Patent number
US05869663

Reaction notes

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