Triethylamine → ROR|At inverse agonist 30

HRID 1505610Notes

Reaction equation

HRID 1505610 reaction equation
[CH:1]1([NH:5][CH2:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:18][CH2:17][N:16]([C:19](=[O:21])[CH3:20])[CH2:15][CH2:14]3)=[CH:9][CH:8]=2)[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:29]1([CH2:35][S:36](Cl)(=[O:38])=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>ClCCl>[C:19]([N:16]1[CH2:15][CH2:14][N:13]([C:10]2[CH:9]=[CH:8][C:7]([CH2:6][N:5]([CH:1]3[CH2:4][CH2:3][CH2:2]3)[S:36]([CH2:35][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:38])=[O:37])=[CH:12][CH:11]=2)[CH2:18][CH2:17]1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74740Phenylmethanesulfonyl chlorideHCID 866906431-(4-(4-((Cyclobutylamino)methyl)phenyl)piperazin-1-yl)ethanone

Product 1

HCID 86690644ROR|At inverse agonist 30Yield 21.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-(4-((cyclobutylamino)methyl)phenyl)piperazin-1-yl)ethanone (185 mg, 0.64 mmol) in dichloromethane (1.5 mL) was added triethylamine (0.18 mL, 1.29 mmol), followed by phenylmethanesulfonyl chloride (185 mg, 0.96 mmol) and the reaction was stirred at ambient temperature for 16 hours. The reaction was then filtered through diatomaceous earth, concentrated and purified by preparative reverse phase HPLC to yield 62 mg of N-[4-(4-Acetyl-piperazin-1-yl)-benzyl]-N-cyclobutyl-C-phenyl-methanesulfonamide. 1H NMR (400 MHz, DMSO) δ 7.46-7.29 (m, 5H), 7.18 (d, J=8.6 Hz, 2H), 6.91 (d, J=8.7 Hz, 2H), 4.36 (s, 2H), 4.18 (s, 2H), 4.14-3.98 (m, 1H), 3.63-3.48 (m, 4H), 3.18-3.10 (m, 2H), 3.10-3.00 (m, 2H), 2.03 (s, 3H), 2.01-1.89 (m, 2H), 1.89-1.72 (m, 2H), 1.54-1.15 (m, 2H); LCMS (m/z) ES+ 442.2 [M+1]+.

Workup

  1. filtrationThe reaction was then filtered through diatomaceous earth
  2. concentrationconcentrated
  3. custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-009f1998778f44569714a0364e517d89
Source dataset
uspto-grants-2015_12
Patent number
US09216988B2

Reaction notes

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