Hydrochloric Acid → HCID 22181238, compound

HRID 1796190Notes

Reaction equation

HRID 1796190 reaction equation
[C:1]([C:4]1[CH:5]=[C:6](/[CH:10]=[CH:11]/[CH2:12][N:13]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[C:20]([C:31](=[O:33])[NH2:32])[CH:19]=2)[S:14]([CH3:17])(=[O:16])=[O:15])[CH:7]=[CH:8][CH:9]=1)(=[NH:3])[NH2:2].C(O[C:37]1[O:38][CH2:39][CH2:40][N:41]=1)C.O1CC(=O)N=[C-]1.C(N(CC)CC)C.[ClH:55]>CO>[ClH:55].[ClH:55].[C:1]([C:4]1[CH:5]=[C:6](/[CH:10]=[CH:11]/[CH2:12][N:13]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH:25]3[CH2:30][CH2:29][N:28]([C:37]4[O:38][CH2:39][CH2:40][N:41]=4)[CH2:27][CH2:26]3)=[C:20]([C:31](=[O:33])[NH2:32])[CH:19]=2)[S:14]([CH3:17])(=[O:16])=[O:15])[CH:7]=[CH:8][CH:9]=1)(=[NH:2])[NH2:3]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 127306402-Ethoxy-4,5-dihydro-1,3-oxazoleHCID 22180972N-[3-(3-amidinophenyl)-2-(E)-propenyl]-N-[3-carbamoyl-4-(piperidin-4-yloxy)phenyl]methanesulfonamideHCID 532495662H-1,3-oxazol-2-id-4-one

Product 1

HCID 22181238HCID 22181238, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[3-(3-amidinophenyl)-2-(E)-propenyl]-N-[3-carbamoyl-4-(piperidin-4-yloxy)phenyl]methanesulfonamide (0.32 g) obtained in example 99(a) in methanol (15 ml) were added successively 2-ethoxy-4,5-dihydrooxazole (0.21 g), which was prepared from 2-oxazolidone according to the method described in Eur. J. Org. Chem., 10, 2645 (1999), and triethylamine (0.56 ml) at room temperature, and the resulting mixture was stirred at room temperature for 2 hours and allowed to stand at room temperature overnight and then evaporated in vacuo. The residue obtained was purified by preparative HPLC (YMC-Pack ODS-A; YMC, eluent: 12% acetonitrile/water). The amorphous solid obtained was dissolved in 1N hydrochloric acid (1.2 ml) and evaporated to dryness in vacuo to afford the title compound (0.15 g, yield: 59%) as a colorless amorphous solid.

Workup

  1. customevaporated in vacuo
  2. customThe residue obtained
  3. customwas purified by preparative HPLC (YMC-Pack ODS-A; YMC, eluent: 12% acetonitrile/water)
  4. customThe amorphous solid obtained
  5. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-2a708e91a13a43d19cf8554f0b6df25b
Source dataset
uspto-grants-2006_04
Patent number
US07030138B2

Reaction notes

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