Tris(hydroxymethyl)aminomethane → 2-chloro-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-4-trifluoromethyl-benzenesulfonamide

HRID 1827533Notes

Reaction equation

HRID 1827533 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][C:20]([O:23][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][O:25]4)=[CH:19][CH:18]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:37][C:38]1[CH:43]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:41]=[CH:40][C:39]=1[S:48](Cl)(=[O:50])=[O:49].[N-]=C=O.C(O)C(N)(CO)CO>C(Cl)Cl>[Cl:37][C:38]1[CH:43]=[C:42]([C:44]([F:46])([F:45])[F:47])[CH:41]=[CH:40][C:39]=1[S:48]([N:15]([C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][N:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)=[CH:14][CH:13]=1)[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)=[CH:19][CH:18]=1)(=[O:50])=[O:49]

Participants

7

Reactant 5

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 8471TriethylamineHCID 105034IsocyanateHCID 27366752-Chloro-4-(trifluoromethyl)benzenesulfonyl chlorideHCID 22137309[4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-amine

Product 1

HCID 221373332-chloro-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-4-trifluoromethyl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-amine (0.060 g, 0.15 mmol) in 0.4 mL methylene chloride was added triethylamine (0.06 mL, 0.45 mmol) and 2-chloro-4-trifluoromethyl benzenesulfonyl chloride (0.084 g, 0.3 mmol). The reaction mixture was stirred at room temperature for 6 days. PS-isocyanate resin (Argonaut Technologies, Foster City, Calif.; 0.050 g) and PS-trisamine resin (Argonaut Technologies; 0.050 g) were added and the reaction mixture was stirred for 2 hr. at room temperature. The resin was filtered off and was washed with methylene chloride. The filtrate was concentrated to give the title compound of Step A. MS 639.4 (M+1)+

Workup

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

Sources & evidence

ORD record
ord-58fef4a7a7bd4670987b00e0c5122b5e
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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