Tris(hydroxymethyl)aminomethane → n-(1-Benzyl-6-chloro-1,2,3,4-tetrahydroquinolin-3-yl)benzenesulfonamide

HRID 1363088Notes

Reaction equation

HRID 1363088 reaction equation
Cl.Cl.[CH2:3]([N:10]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[CH2:13][CH:12]([NH2:21])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CN1CCOCC1.[C:29]1([S:35](Cl)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(O)C(N)(CO)CO>ClCCCl>[CH2:3]([N:10]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[CH2:13][CH:12]([NH:21][S:35]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)(=[O:37])=[O:36])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 7369Benzenesulfonyl chlorideHCID 79724-MethylmorpholineHCID 1317281071-Benzyl-6-chloro-1,2,3,4-tetrahydroquinolin-3-amine, dihydrochloride

Product 1

HCID 11373308n-(1-Benzyl-6-chloro-1,2,3,4-tetrahydroquinolin-3-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

The title compound was synthesized as part of library using the following procedure in a parallel synthesis fashion using 48 well red and blue minireactors. Typical procedure: To a solution of 22B (14 mg, 0.05 mmol) in DCE (0.5 mL) at RT was added NMM (0.109 mL, 0.1 mmol), followed by addition of benzene sulfonylchloride (17.6 mg, 0.1 mmol) in DCE (0.5 μL). The reaction mixture was shaken at RT for 24 h, and treated with 100 mg of PS-Trisamine (4 mmol/g loading) for 2 h to remove excess sulfonyl chloride. Contents were filtered into a synthesis tube rack (STR) and the solvent was dried in a speed vac. The resulting residue was chromatographed using Prep HPLC (conditions: Xterra MS-C18 (30×50 mm); Eluted with 10% to 100% B, 6 min gradient. (A=100% water−0.1% TFA and B=acetonitrile with 0.1% TFA); Flow rate at 30 mL/min. UV detection at 220 nm) to give compound 50 (13.8 mg, 69%). HPLC: 99% at 1.74 min (retention time) (Conditions: Xterra MS-C18 (2.1×50 mm); Eluted with 0% to 100% B, 2.75 min gradient. (A=100% water−0.1% TFA and B=acetonitrile with 0.1% TFA); Flow rate at 1 mL/min. UV detection at 220 nm). MS (ES): m/z 413 [M+H]+.

Workup

  1. customto remove excess sulfonyl chloride
  2. filtrationContents were filtered into a synthesis tube rack (STR)
  3. customthe solvent was dried in a speed vac
  4. customThe resulting residue was chromatographed
  5. washEluted with 10% to 100% B, 6 min gradient

Sources & evidence

ORD record
ord-954ab978099149e18620c5b6c0fd9121
Source dataset
uspto-grants-2011_02
Patent number
US07884113B2

Reaction notes

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