Hydrochloric Acid → HCID 131720059, compound

HRID 1601926Notes

Reaction equation

HRID 1601926 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:31][CH2:32]OS(C)(=O)=O)[CH2:14][N:13]([CH2:15][C:16]3[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=3)[C:12](=[O:30])[CH2:11][O:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[N:38]1([CH:44]2[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1.O.[ClH:51]>CN(C=O)C.CCOCC>[OH2:10].[ClH:51].[ClH:51].[F:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:31][CH2:32][N:47]3[CH2:48][CH2:49][CH:44]([N:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)[CH2:45][CH2:46]3)[CH2:14][N:13]([CH2:15][C:16]3[CH:21]=[C:20]([C:22]([F:23])([F:25])[F:24])[CH:19]=[C:18]([C:26]([F:27])([F:29])[F:28])[CH:17]=3)[C:12](=[O:30])[CH2:11][O:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[F:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:31][CH2:32][N:47]3[CH2:48][CH2:49][CH:44]([N:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)[CH2:45][CH2:46]3)[CH2:14][N:13]([CH2:15][C:16]3[CH:21]=[C:20]([C:22]([F:23])([F:25])[F:24])[CH:19]=[C:18]([C:26]([F:27])([F:29])[F:28])[CH:17]=3)[C:12](=[O:30])[CH2:11][O:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[ClH:51].[ClH:51]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 786071,4'-BipiperidineHCID 21200578HCID 21200578, compound

Product 1

HCID 131720059HCID 131720059, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 0.86 g of the compound obtained in step C of EXAMPLE 26 and 0.7 g of 4-(piperid-1-yl)piperidine in 3 ml of DMF is heated at 70° C. for 4 hours 30 minutes. After cooling to RT, the reaction mixture is poured into water and extracted with AcOEt, the organic phase is washed with 1 N 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.=260° C. (dec.).

Workup

  1. temperatureAfter cooling to RT
  2. extractionextracted with AcOEt
  3. washthe organic phase is washed with 1 N 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-a424076da14846008cfaae5e56391201
Source dataset
uspto-grants-1999_11
Patent number
US05977359

Reaction notes

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