Hydrochloric Acid → HCID 44599584, compound

HRID 510654Notes

Reaction equation

HRID 510654 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([NH:18][C:19]([C:21]3[CH:42]=[CH:41][C:24]([O:25][C:26]4[CH:35]=[C:34]5[C:29]([CH:30]([C:36]([OH:38])=[O:37])[CH2:31][CH2:32][O:33]5)=[CH:28][C:27]=4[C:39]#[N:40])=[CH:23][CH:22]=3)=[O:20])=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.[ClH:43]>O1CCOCC1>[ClH:43].[C:39]([C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][C:26]=1[O:25][C:24]1[CH:23]=[CH:22][C:21]([C:19](=[O:20])[NH:18][C:12]3[CH:11]=[C:10]4[C:15]([CH2:16][CH2:17][NH:8][CH2:9]4)=[CH:14][CH:13]=3)=[CH:42][CH:41]=1)[O:33][CH2:32][CH2:31][CH:30]2[C:36]([OH:38])=[O:37])#[N:40]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67080406HCID 67080406, compound

Product 1

HCID 44599584HCID 44599584, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of 7-(4-(2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinolin-7-ylcarbamoyl)phenoxy)-6-cyanochroman-4-carboxylic acid (40 mg, 0.070 mmol) in dioxane (1 mL) at ambient temperature was added a 4M solution of hydrogen chloride in dioxane (2 mL). The resulting solution was stirred at ambient temperature for 90 minutes. Some dark material had separated from the cloudy reaction mixture, and the supernatant was concentrated to afford 6-cyano-7-(4-(1,2,3,4-tetrahydroisoquinolin-7-ylcarbamoyl)phenoxy)chroman-4-carboxylic acid hydro-chloride as a light tan solid (30 mg, 84% yield). MS (apci) m/z=470.2 (M-Cl).

Workup

  1. customSome dark material had separated from the cloudy reaction mixture
  2. concentrationthe supernatant was concentrated

Sources & evidence

ORD record
ord-9aec5ae216c24eb091cdda6351e263fc
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

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