Triethylamine → HCID 86686000, compound

HRID 2277706Notes

Reaction equation

HRID 2277706 reaction equation
[NH2:1][CH:2]1[C:11]2[CH:10]=[N:9][CH:8]=[C:7]([N:12]3[CH2:20][C:19]4[C:14](=[CH:15][CH:16]=[C:17]([Cl:21])[CH:18]=4)[C:13]3=[O:22])[C:6]=2[CH2:5][CH2:4][CH2:3]1.CCN(CC)CC.[CH2:30]([S:32](Cl)(=[O:34])=[O:33])[CH3:31]>C(Cl)Cl>[Cl:21][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:22])[N:12]([C:7]1[C:6]3[CH2:5][CH2:4][CH2:3][CH:2]([NH:1][S:32]([CH2:30][CH3:31])(=[O:34])=[O:33])[C:11]=3[CH:10]=[N:9][CH:8]=1)[CH2:20]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 86686001HCID 86686001, compound

Product 1

HCID 86686000HCID 86686000, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(8-amino-5,6,7,8-tetrahydro-isoquinolin-4-yl)-5-chloro-2,3-dihydro-isoindol-1-one (156 mg, 0.5 mmol) and Et3N (210 uL) in DCM (10 mL) was added ethanesulfonyl chloride (48 uL mg, 0.5 mmol) at 0° C. and stirring continued at 0° C. for 1 h. The resulting mixture was extracted with EtOAc (2×50 mL). Combined organics were washed with brine, dried over Na2SO4, filtered and concentrated to afford the title compound. The residue was separated by prep-HPLC to give a racemic mixture of title compound (170 mg, 84%) as a light yellow solid. MS: 406.1 (M+H+).

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (2×50 mL)
  2. washCombined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b3dff2e57dea46968b24798a14ef78c0
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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