Triethylamine → 2-Cyano-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-benzenesulfonamide

HRID 1827549Notes

Reaction equation

HRID 1827549 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][O:25]4)[CH:18]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:37]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[S:45](Cl)(=[O:47])=[O:46])#[N:38].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:37]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[S:45]([N:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][N:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)=[CH:10][CH:11]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH:18]=1)(=[O:47])=[O:46])#[N:38]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5223472-Cyanobenzenesulfonyl ChlorideHCID 22137433[4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-amine

Product 1

HCID 221372832-Cyano-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-amine (0.091 g, 0.23 mmol) and triethylamine (0.097 mL, 0.69 mmol) in 2 mL methylene chloride was added 2-cyanobenzenesulfonyl chloride (0.093 g, 0.46 mmol). The reaction mixture was stirred at room temperature for 24 hr. Saturated aqueous sodium bicarbonate was added and the layers were separated. The aqueous layer was washed with an additional 2 mL of methylene chloride. The combined organic layers were concentrated to afford the title compound of Step A.

Workup

  1. customthe layers were separated
  2. washThe aqueous layer was washed with an additional 2 mL of methylene chloride
  3. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-b687e3e9f1574b49a08d89f017c2da74
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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