Hydrochloric Acid → HCID 67391000, compound

HRID 1040528Notes

Reaction equation

HRID 1040528 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][C@@H:7]([NH:10][C:11](=[O:44])[C@@H:12]([NH:14][C:15]([C:17]2[N:21]3[C@@:22]([CH2:35][C:36]4[CH:41]=[CH:40][C:39]([C:42]#[N:43])=[CH:38][CH:37]=4)([CH3:34])[C:23](=[O:33])[N:24]([C:25]4[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=4)[C:20]3=[N:19][CH:18]=2)=[O:16])[CH3:13])[CH2:6]1)=[O:4].Cl.O1CCOCC1>>[C:42]([C:39]1[CH:40]=[CH:41][C:36]([CH2:35][C@@:22]2([CH3:34])[N:21]3[C:17]([C:15]([NH:14][C@@H:12]([CH3:13])[C:11]([NH:10][C@@H:7]4[CH2:8][CH2:9][C@@H:5]([C:3]([OH:4])=[O:2])[CH2:6]4)=[O:44])=[O:16])=[CH:18][N:19]=[C:20]3[N:24]([C:25]3[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=3)[C:23]2=[O:33])=[CH:37][CH:38]=1)#[N:43]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 312751,4-DioxaneHCID 67389654HCID 67389654, compound

Product 1

HCID 67391000HCID 67391000, compoundYield 61.2%

Conditions

Temperature
100 °C

Procedure

To (1R,3R)-3-((S)-2-{[(R)-5-(4-cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-propionylamino)-cyclopentanecarboxylic acid methyl ester (35.1 mg, 0.055 mmol) were added 1N HCl in 1,4-dioxane (1 mL, 1 mmol) and 1N HCl (0.5 mL, 0.5 mmol). The reaction tube was sealed and the reaction solution was stirred at 100° C. for 1 h. The reaction solution was then cooled to room temperature, filtered, and was purified by reverse phase HPLC to afford 21 mg of the title compound as a white solid, m/z 623.1 [M+1]+.

Workup

  1. customThe reaction tube was sealed
  2. temperatureThe reaction solution was then cooled to room temperature
  3. filtrationfiltered
  4. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-edad5a9b89ad4c6590a43532a80e6fae
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

Loading…