Hydrochloric Acid → HCID 178479318, compound

HRID 1757012Notes

Reaction equation

HRID 1757012 reaction equation
C(OC([NH:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][N:23]([C:26]([NH:28][C@H:29]3[CH2:34][CH2:33][C@H:32]([C:35]([O:37][CH2:38][C:39]([N:41]4[CH2:46][CH2:45][O:44][CH2:43][CH2:42]4)=[O:40])=[O:36])[CH2:31][CH2:30]3)=[O:27])[CH2:22][CH2:21]2)=[CH:16][CH:15]=1)=[NH:13])=O)C1C=CC=CC=1.[ClH:47]>CN(C)C=O.[Pd]>[ClH:47].[C:12]([C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:21][CH2:22][N:23]([C:26]([NH:28][C@H:29]3[CH2:30][CH2:31][C@H:32]([C:35]([O:37][CH2:38][C:39]([N:41]4[CH2:46][CH2:45][O:44][CH2:43][CH2:42]4)=[O:40])=[O:36])[CH2:33][CH2:34]3)=[O:27])[CH2:24][CH2:25]2)=[CH:16][CH:15]=1)(=[NH:11])[NH2:13]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178512411HCID 178512411, compound

Product 1

HCID 178479318HCID 178479318, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 300 mg of 1-[4-(N-benzyloxycarbonyl-amidino)-phenyl]-4-[N-[trans-4-[(morpholinocarbonyl)-methoxycarbonyl]-cyclohexyl]-aminocarbonyl]-piperazine in 20 ml dimethylformamide is hydrogenated for 2 hours in the presence of 0.3 g of a catalyst consisting of 10% palladium on activated charcoal under an excess hydrogen pressure of 5 bar. Ethereal hydrochloric acid is added and the mixture is filtered. The filtrate is evaporated down under reduced pressure and the residue remaining is triturated with ether/acetone, acetone and acetone/methylene chloride and suction filtered. Yield: 210 mg (83% of theory), Rf value: 0.27 (silica gel; methylene chloride/methanol/conc. ammonia=4:1:0.25)

Workup

  1. filtrationthe mixture is filtered
  2. customThe filtrate is evaporated down under reduced pressure
  3. customthe residue remaining is triturated with ether/acetone, acetone and acetone/methylene chloride and suction
  4. filtrationfiltered

Sources & evidence

ORD record
ord-79c050b236e5425a839b377b075104b3
Source dataset
uspto-grants-1995_08
Patent number
US05442064

Reaction notes

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