Triethylamine → HCID 66616453, compound

HRID 1889636Notes

Reaction equation

HRID 1889636 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:16][N:17]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH:8]=1.CCN(CC)CC.[Cl:43][C:44]1[C:45]([OH:55])=[C:46]([S:51](Cl)(=[O:53])=[O:52])[CH:47]=[C:48]([Cl:50])[CH:49]=1>C(Cl)Cl>[Cl:43][C:44]1[C:45]([OH:55])=[C:46]([S:51]([NH:1][CH2:2][C:3]2[CH:8]=[C:7]([C:9]3[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=3)[CH:6]=[C:5]([CH2:16][N:17]([CH2:28][C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=3)[S:18]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:4]=2)(=[O:53])=[O:52])[CH:47]=[C:48]([Cl:50])[CH:49]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideHCID 58531526HCID 58531526, compound

Product 1

HCID 66616453HCID 66616453, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-((5-(aminomethyl)-4′-fluorobiphenyl-3-yl)methyl)-N-(4-fluorobenzyl)-4-methylbenzenesulfonamide (40 mg, 0.081 mmol) and Et3N (40 mg, 0.395 mmol) in CH2Cl2 (4 mL) at rt was added solid 3,5-dichloro-2-hydroxybenzene-1-sulfonyl chloride (21.24 mg, 0.081 mmol) with stirring. The reaction was complete within an hour. The mixture was concentrated and the residue was purified by prep HPLC to provide the desired product as a white solid (30 mg). 1H NMR (CDCl3): δ 7.72 (d, J=8.2 Hz, 2H), 7.51 (d, J=2.2 Hz, 1H), 7.34-6.83 (m, 14H), 5.32 (t, J=6.0 Hz, 1H), 4.25 (s, 2H), 4.245 (s, 2H), 4.12 (d, J=6.0 Hz, 2H), 2.43 (s, 3H); MS (ESI): (M+H)+=717.

Workup

  1. waitThe reaction was complete within an hour
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-8725b57357b840429fad46686453bda5
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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