5-Isoquinolinesulfonyl chloride → HCID 67151686, compound

HRID 1805229Notes

Reaction equation

HRID 1805229 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:24]1[C:33]2[CH:32]=[CH:31][CH:30]=[C:29]([S:34](Cl)(=[O:36])=[O:35])[C:28]=2[CH:27]=[CH:26][N:25]=1>O1CCCC1.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([NH:21][S:34]([C:29]3[C:28]4[CH:27]=[CH:26][N:25]=[CH:24][C:33]=4[CH:32]=[CH:31][CH:30]=3)(=[O:35])=[O:36])=[CH:19][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 33716555-Isoquinolinesulfonyl chlorideHCID 66705807HCID 66705807, compound

Product 1

HCID 67151686HCID 67151686, compoundYield 64.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

(S)-4-[2-(4-Amino-phenyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (150 mg) was dissolved in tetrahydrofuran at room temperature before treatment with triethylamine (129.8 μl) and isoquinoline-5-sulfonyl chloride (141.4 mg), the reaction mixture was then warmed to 50° C. and stirred for 6 hours. Upon evaporation of the solvent in vacuo the residue was purified by flash column chromatography (SiO2; hexane/EtOAc 3:1) to afford title compound (S)-4-{2-[4-(isoquinoline-5-sulfonylamino)-phenyl]-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (155 mg) as a white solid. MS (ISP): 512.3 ([M+H]+).

Workup

  1. customUpon evaporation of the solvent in vacuo the residue
  2. customwas purified by flash column chromatography (SiO2; hexane/EtOAc 3:1)

Sources & evidence

ORD record
ord-be16c1142aaa4bc6bb08464b0321658d
Source dataset
uspto-grants-2013_01
Patent number
US08354441B2

Reaction notes

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