Triethylamine → 2,4-dichloro-N-[2-chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzenesulfonamide

HRID 1827540Notes

Reaction equation

HRID 1827540 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)[CH:21]=[CH:20][C:3]=1[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:8][CH:7]=1.C(N(CC)CC)C.[Cl:38][C:39]1[CH:44]=[C:43]([Cl:45])[CH:42]=[CH:41][C:40]=1[S:46](Cl)(=[O:48])=[O:47].[N-]=C=O>C(Cl)Cl>[Cl:38][C:39]1[CH:44]=[C:43]([Cl:45])[CH:42]=[CH:41][C:40]=1[S:46]([N:5]([CH2:4][C:3]1[CH:20]=[CH:21][C:22]([O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)=[CH:23][C:2]=1[Cl:1])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)=[CH:8][CH:7]=1)(=[O:48])=[O:47]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 105034IsocyanateHCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 22137435(2-Chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

Product 1

HCID 221374052,4-dichloro-N-[2-chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzenesulfonamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [2-chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine (0.060 g, 0.15 mmol) in 0.4 mL methylene chloride was added triethylamine (0.06 mL, 0.45 mmol) and 2,4-dichlorobenzenesulfonyl chloride (0.074 g, 0.3 mmol). The reaction mixture was stirred at room temperature for 6 days. PS-isocyanate resin (0.050 g) and PStrisamine resin (0.050 g) were added and the reaction mixture was stirred for 2 hr. at room temperature. The resin was filtered off with the aid of methylene chloride. The filtrate was concentrated to afford the title compound of Step A (0.096 g). MS 639.3 (M+1)+

Workup

  1. stirringthe reaction mixture was stirred for 2 hr
  2. customat room temperature
  3. filtrationThe resin was filtered off with the aid of methylene chloride
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-73a79e1480034d0c95e7f86040ccb2f7
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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