Triethylamine → HCID 86659762, compound

HRID 1889650Notes

Reaction equation

HRID 1889650 reaction equation
[Cl:1][C:2]1[C:3]([OH:13])=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH2:14][CH2:15][C:16]1[CH:17]=[C:18]([CH:41]=[C:42]([O:44][C:45]2[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=2)[CH:43]=1)[CH2:19][N:20]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)[S:21]([C:24]1[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[C:25]=1[OH:32])(=[O:23])=[O:22].CCN(CC)CC>C(Cl)Cl>[Cl:31][C:26]1[C:25]([OH:32])=[C:24]([S:21]([N:20]([CH2:19][C:18]2[CH:41]=[C:42]([O:44][C:45]3[CH:46]=[CH:47][C:48]([F:51])=[CH:49][CH:50]=3)[CH:43]=[C:16]([CH2:15][NH:14][S:9]([C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=3[OH:13])(=[O:10])=[O:11])[CH:17]=2)[CH2:33][C:34]2[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=2)(=[O:23])=[O:22])[CH:29]=[C:28]([Cl:30])[CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideHCID 58531469HCID 58531469, compound

Product 1

HCID 86659762HCID 86659762, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,5-dichloro-2-hydroxybenzene-1-sulfonyl chloride (27.1 mg, 0.104 mmol) in 4 mL of CH2Cl2 was added solid N-(3-(aminomethyl)-5-(4-fluorophenoxy)benzyl)-3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxybenzenesulfonamide (60 mg, 0.104 mmol) followed by Et3N (110 μL) at rt. The mixture was stirred at rt for 45 min. Direct purification of the reaction mixture by prep HPLC provided the desired product (71 mg, 85%). 1H NMR (CD3OD): δ 7.68 (s, 1H), 7.60 (s, 1H), 7.49 (s, 2H), 7.13˜6.90 (m, 8H), 6.67 (s, 1H), 6.61 (s, 1H), 6.45 (s, 1H), 4.44 (s, 2H), 4.30 (s, 2H), 4.08 (s, 2H); MS (ESI): (M+H)+=805.

Workup

  1. customDirect purification of the reaction mixture by prep HPLC

Sources & evidence

ORD record
ord-613ee08f04424796bf1b107183a3c66f
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

Loading…