Hydrochloric Acid → HCID 22181086, compound

HRID 1796189Notes

Reaction equation

HRID 1796189 reaction equation
[ClH:1].Cl.[C:3]([C:6]1[CH:7]=[C:8](/[CH:12]=[CH:13]/[CH2:14][N:15]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[C:23]([C:34](=[O:36])[NH2:35])[CH:22]=2)[S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])[CH:9]=[CH:10][CH:11]=1)(=[NH:5])[NH2:4].CO[C:39]1[CH2:40][CH2:41][CH2:42][N:43]=1.N1CCCC1=O.Cl>C(O)C.O.C(N(CC)CC)C>[ClH:1].[ClH:1].[C:3]([C:6]1[CH:7]=[C:8](/[CH:12]=[CH:13]/[CH2:14][N:15]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH:28]3[CH2:33][CH2:32][N:31]([C:39]4[CH2:40][CH2:41][CH2:42][N:43]=4)[CH2:30][CH2:29]3)=[C:23]([C:34](=[O:36])[NH2:35])[CH:22]=2)[S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])[CH:9]=[CH:10][CH:11]=1)(=[NH:4])[NH2:5]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 120252-PyrrolidoneHCID 3534432-Methoxy-1-Pyrroline2×HCID 22181059N-[3-(3-amidinophenyl)-2-(E)-propenyl]-N-[3-carbamoyl-4-(piperidin-4-yloxy)phenyl]ethanesulfonamide dihydrochloride

Product 1

HCID 22181086HCID 22181086, compoundYield 147%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 8471TriethylamineSolvent2×

Procedure

To a solution of N-[3-(3-amidinophenyl)-2-(E)-propenyl]-N-[3-carbamoyl-4-(piperidin-4-yloxy)phenyl]ethanesulfonamide dihydrochloride (0.68 g) obtained in example 100(a) in ethanol (15 ml) were added successively 5-methoxy-3,4-dihydro-2H-pyrrole (0.36 g), which was prepared from 2-pyrrolidinone according to the method described in Org. Prep. Proced. Int., 24, 147 (1992), and triethylamine (0.85 ml) at room temperature and the resulting mixture was allowed to stand at room temperature overnight. At the end of this time, to the reaction mixture were furthermore added successively 5-methoxy-3,4-dihydro-2H-pyrrole (0.19 g) and triethylamine (0.34 ml) at room temperature, and the resulting mixture was stirred at room temperature for 5 hours and then evaporated in vacuo. Subsequently, to the residue obtained were successively added ethanol (10 ml) and a 4N solution of hydrogen chloride in dioxane (4 ml), and the resulting mixture was evaporated in vacuo. The residue obtained was purified by preparative HPLC (YMC-Pack ODS-A; YMC, eluent: 10% acetonitrile/water). To the amorphous solid obtained was added 1N hydrochloric acid (8 ml) and the resulting mixture was evaporated to dryness in vacuo. The residue obtained was dissolved in water and then lyophilized to afford the title compound (0.56 g, yield: 73%) as a pale brown amorphous solid.

Workup

  1. customat room temperature
  2. customevaporated in vacuo
  3. customSubsequently, to the residue obtained
  4. customa 4N solution of hydrogen chloride in dioxane (4 ml), and the resulting mixture was evaporated in vacuo
  5. customThe residue obtained
  6. customwas purified by preparative HPLC (YMC-Pack ODS-A; YMC, eluent: 10% acetonitrile/water)
  7. customTo the amorphous solid obtained
  8. customthe resulting mixture was evaporated to dryness in vacuo
  9. customThe residue obtained

Sources & evidence

ORD record
ord-b63bde726bb94a3d83ef435261123fde
Source dataset
uspto-grants-2006_04
Patent number
US07030138B2

Reaction notes

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