Hydrochloric Acid → HCID 58431148, compound

HRID 1040547Notes

Reaction equation

HRID 1040547 reaction equation
Cl.O1CCOCC1.[C:8]([C:10]1[CH:52]=[CH:51][C:13]([CH2:14][C@@:15]2([CH3:50])[N:19]3[C:20]([C:23]([NH:25][C:26]4([C:29]([NH:31][C@@H:32]5[CH2:36][CH2:35][C@H:34]([C:37]([O:39]C)=[O:38])[CH2:33]5)=[O:30])[CH2:28][CH2:27]4)=[O:24])=[CH:21][N:22]=[C:18]3[N:17]([C:41]3[CH:46]=[C:45]([Cl:47])[CH:44]=[C:43]([Cl:48])[CH:42]=3)[C:16]2=[O:49])=[CH:12][CH:11]=1)#[N:9]>>[C:8]([C:10]1[CH:52]=[CH:51][C:13]([CH2:14][C@@:15]2([CH3:50])[N:19]3[C:20]([C:23]([NH:25][C:26]4([C:29]([NH:31][C@@H:32]5[CH2:36][CH2:35][C@H:34]([C:37]([OH:39])=[O:38])[CH2:33]5)=[O:30])[CH2:27][CH2:28]4)=[O:24])=[CH:21][N:22]=[C:18]3[N:17]([C:41]3[CH:46]=[C:45]([Cl:47])[CH:44]=[C:43]([Cl:48])[CH:42]=3)[C:16]2=[O:49])=[CH:12][CH:11]=1)#[N:9]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 312751,4-DioxaneHCID 58431021HCID 58431021, compound

Product 1

HCID 58431148HCID 58431148, compoundYield 67.3%

Conditions

Temperature
100 °C

Procedure

1N HCl in 1,4-dioxane (1 mL, 1 mmol) and 1N HCl (aq.) (0.5 mL, 0.5 mmol) were added to methyl (1S,3R)-3-({[1-({[(3R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[1,2-a]imidazol-5-yl]carbonyl}amino)cyclopropyl]-carbonyl}amino)cyclopentanecarboxylate (35 mg, 0.054 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 purified via reverse phase HPLC. The title compound (23.1 mg) was isolated as a white solid, m/z 635.1 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-af1a659b82284ed69b0fe48a75b00f23
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

Loading…