1,4-Dioxane → HCID 68284169, compound

HRID 1527557Notes

Reaction equation

HRID 1527557 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([C:13](=[O:23])[NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[N:9]1[C:24](=[O:38])[CH2:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]([C:35](=[O:37])[NH2:36])[CH:27]=1)=O)(C)(C)C.O1CCOCC1>Cl>[Cl:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[CH2:15][NH:14][C:13]([CH:10]1[N:9]([C:24](=[O:38])[CH2:25][C:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]([C:35]([NH2:36])=[O:37])[CH:27]=2)[NH:8][CH2:12][CH2:11]1)=[O:23]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 68283426HCID 68283426, compound

Product 1

HCID 68284169HCID 68284169, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-[2-(1-carbamoyl-1H-indol-3-yl)-acetyl]-3-(3-chloro-benzylcarbamoyl)-pyrazolidine-1-carboxylic acid tert-butyl ester (15 mg, 0.03 mmol) in HCl 4N in dioxane (69.4 μL, 0.278 mmol) was stirred at 23° C. for 1 h. The crude material was directly purified by preparative HPLC (waters SunFire C18 ODB 5 um, 19×50, 5-100% CH3CN/H2O/15 min, 100% CH3CN/2.5 min, CH3CN and H2O containing 0.1% of TFA, flow: 20 mL/min) to give after lyophilization of the purified fractions the desired material. MS (LC-MS): 440 [M+H]+; tR (HPLC conditions b): 3.49 min.

Workup

  1. customThe crude material was directly purified by preparative HPLC (waters SunFire C18 ODB 5 um, 19×50, 5-100% CH3CN/H2O/15 min, 100% CH3CN/2.5 min, CH3CN and H2O containing 0.1% of TFA, flow: 20 mL/min)
  2. customto give after lyophilization of the
  3. custompurified fractions the desired material
  4. custom3.49 min.

Sources & evidence

ORD record
ord-27b6ed236e1e474eaf231a5ea1fa5b29
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…