Hydrochloric Acid → HCID 86686003, compound

HRID 2277710Notes

Reaction equation

HRID 2277710 reaction equation
[NH2:1][CH:2]1[C:11]2[CH:10]=[N:9][CH:8]=[C:7]([N:12]3[CH:20]([CH2:21][CH3:22])[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([Cl:23])[CH:18]=4)[C:13]3=[O:24])[C:6]=2[CH2:5][CH2:4][CH2:3]1.CCN(CC)CC.[CH3:32][S:33](Cl)(=[O:35])=[O:34].Cl>C(Cl)Cl.O1CCOCC1>[Cl:23][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:24])[N:12]([C:7]1[C:6]3[CH2:5][CH2:4][CH2:3][CH:2]([NH:1][S:33]([CH3:32])(=[O:35])=[O:34])[C:11]=3[CH:10]=[N:9][CH:8]=1)[CH:20]2[CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86686002HCID 86686002, compound

Product 1

HCID 86686003HCID 86686003, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-(8-amino-5,6,7,8-tetrahydro-isoquinolin-4-yl)-5-chloro-3-ethyl-2,3-dihydro-isoindol-1-one (511.5 mg, 1.5 mmol) in DCM (15 mL) was added Et3N (3 mmol) and methanesulfonyl chloride (228 mg, 2 mmol) at 0° C. The resulting reaction mixture was stirred at room temperature for 1 hour before it was poured into 1 N HCl in dioxane (15 mL) and washed with EtOAc (15 mL×2). After the organic layer was decanted, the aqueous layer was basified to pH>8 with satd. aq. NaHCO3 solution. After extracted with EtOAc (20 mL×2), the combined organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give the title compound (228 mg, 62%) as a mixture of four diastereomers. MS: 420.1 (M+H+).

Workup

  1. customThe resulting reaction mixture
  2. washwashed with EtOAc (15 mL×2)
  3. customAfter the organic layer was decanted
  4. extractionAfter extracted with EtOAc (20 mL×2)
  5. washthe combined organic layers were washed with brine
  6. customdried over anhy
  7. filtrationNa2SO4, filtered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a95100c88f0b4b45a95011bd7ef872aa
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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