Hydrochloric Acid → HCID 86709723, compound

HRID 2285427Notes

Reaction equation

HRID 2285427 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C@H:12]([NH:14][S@@](C(C)(C)C)=O)[CH3:13])=[CH:7][CH:6]=2.Cl.O1CCOCC1>CO>[ClH:1].[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C@H:12]([NH2:14])[CH3:13])=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 89948743HCID 89948743, compound

Product 1

HCID 86709723HCID 86709723, compoundYield 213.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (R,R)-2-methyl-propane-2-sulfinic acid [1-(3-chloro-isoquinolin-6-yl)-ethyl]-amide (932 mg, 3 mmol) in methanol (9 mL) was stirred at room temperature under nitrogen. 4M HCl in dioxane (3 mL, 12 mmol) was added and the reaction mixture was stirred at room temperature for 30 minutes. The solvent was evaporated and the residue was triturated with ether. The orange solid was collected, washed with ether and dried to afford the title compound (777 mg). 1H NMR (300 MHz, d6-DMSO) δ 1.61 (d, J=6.7 Hz, 3H), 4.58-4.67 (m, 1H), 7.90 (dd, J=8.5, 1.4 Hz, 1H), 8.04 (br, 1H), 8.05 (br, 1H), 8.26 (d, J=8.5, 1H), 8.65-8.8 (br, 3H), 9.25 (s, 1H). LCMS (m/z) 207/209 [M+H], Tr 0.72 minutes.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was triturated with ether
  3. customThe orange solid was collected
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-18ced79d6b784a3f826344d18812b07d
Source dataset
uspto-grants-2015_09
Patent number
US09145441B2

Reaction notes

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