Triethylamine → HCID 66970725, compound

HRID 1360651Notes

Reaction equation

HRID 1360651 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([S:12]([CH2:15][CH:16](O)[CH2:17][CH2:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)(=[O:14])=[O:13])[CH2:9]2)=[CH:4][CH:3]=1.CCN(CC)CC.CS(Cl)(=O)=O>C1COCC1.C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([S:12]([CH:15]=[CH:16][CH2:17][CH2:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)(=[O:14])=[O:13])[CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57855497HCID 57855497, compound

Product 1

HCID 66970725HCID 66970725, compoundYield 116.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-[(7-chloro-3,4-dihydroisoquinolin-2(1H)-yl)sulfonyl]-4-pyridin-3-ylbutan-2-ol (270 mg of crude compound) and Et3N (0.23 ml, 1.69 mmol) in anhydrous THF (3 ml) was cooled at 0° C., then methanesulfonyl chloride (0.066 ml, 0.85 mmol) was added dropwise. The resulting mixture was stirred at 0° C. for 1 hour, then at 60° C. for 15 hours. The reaction mixture was diluted with DCM, then washed with a saturated aqueous solution of NaHCO3 and brine. The organic layer was dried (MgSO4) and the solvents were removed under reduced pressure to give the title compound as an oil (300 mg) used in the next step without further purification. HPLC, Rt: 3.1 min (purity: 63%). LC/MS, M+(ESI): 363.2, M−(ESI): 361.1.

Workup

  1. waitat 60° C. for 15 hours
  2. washwashed with a saturated aqueous solution of NaHCO3 and brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-320abb795baa4378aba3f4430909a9f5
Source dataset
uspto-grants-2011_02
Patent number
US07879876B2

Reaction notes

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