Hydrochloric Acid → HCID 69820673, compound

HRID 1840515Notes

Reaction equation

HRID 1840515 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C@H:11]([NH:22][S:23]([C:26]2[CH:31]=[C:30](Br)[CH:29]=[C:28]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=3)[C:27]=2[NH:39][C:40](=[O:43])[CH2:41][CH3:42])(=[O:25])=[O:24])[C:12]([CH:14]2[CH:19]([CH2:20][CH3:21])[CH2:18][CH2:17][NH:16][CH2:15]2)=[O:13])=[CH:4][CH:3]=1.C([O-])=O.[NH4+].[ClH:48]>CO.C(O)(C)C.[Pd]>[ClH:48].[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C@H:11]([NH:22][S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=3)[C:27]=2[NH:39][C:40](=[O:43])[CH2:41][CH3:42])(=[O:25])=[O:24])[C:12]([CH:14]2[CH:19]([CH2:20][CH3:21])[CH2:18][CH2:17][NH:16][CH2:15]2)=[O:13])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 2723923Ammonium formateHCID 69820417HCID 69820417, compound

Product 1

HCID 69820673HCID 69820673, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 0.2 g (0.3 mmol) of (S)-N-[2-[[[4-(6-aminopyrid-3-yl)-1-[(4-ethylpiperid-3-yl)carbonyl]butyl]amino]sulphonyl]-4-bromo-6-pyrid-2-ylphenyl]propanamide, 0.02 g of active 10% palladium-on-charcoal and 0.2 g of ammonium formate (3.0 mmol) in 10 ml of methanol is refluxed for 2 h. The reaction mixture is filtered and is then taken up in 100 ml of dichloromethane, washed with 50 ml of saturated sodium hydrogen carbonate solution and 50 ml of saturated sodium chloride solution. The resulting solution is dried over sodium sulphate and then filtered and the resulting product is concentrated. The residue thus obtained is taken up in 40 ml of a 0.1N solution of hydrogen chloride in isopropanol and is then concentrated and purified by chromatography on an RP18 column, eluting with an acetonitrile/water gradient of from 5/95 to 30/70. 0.135 g of (S)-N-[2-[[[4-(6-aminopyrid-3-yl)-1-[(4-ethylpiperid-3-yl)carbonyl]butyl]amino]sulphonyl]-6-pyrid-2-ylphenyl]propanamide hydrochloride (2:1) is obtained.

Workup

  1. temperatureis refluxed for 2 h
  2. filtrationThe reaction mixture is filtered
  3. washwashed with 50 ml of saturated sodium hydrogen carbonate solution and 50 ml of saturated sodium chloride solution
  4. dry with materialThe resulting solution is dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationthe resulting product is concentrated
  7. customThe residue thus obtained
  8. concentrationis then concentrated
  9. custompurified by chromatography on an RP18 column
  10. washeluting with an acetonitrile/water gradient of from 5/95 to 30/70

Sources & evidence

ORD record
ord-390c21f0187042d0bcf0128f5e037c02
Source dataset
uspto-grants-2004_01
Patent number
US06680329B2

Reaction notes

Loading…