Tris(hydroxymethyl)aminomethane → HCID 22137401, compound

HRID 1827562Notes

Reaction equation

HRID 1827562 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][CH:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][O:26]4)=[CH:20][CH:19]=3)[CH3:17])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:38]1([CH3:50])[CH:43]=[C:42]([CH3:44])[CH:41]=[C:40]([CH3:45])[C:39]=1[S:46](Cl)(=[O:48])=[O:47].[N-]=C=O.C(O)C(N)(CO)CO>C(Cl)Cl>[CH3:50][C:38]1[CH:43]=[C:42]([CH3:44])[CH:41]=[C:40]([CH3:45])[C:39]=1[S:46]([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)[CH:16]([C:18]1[CH:19]=[CH:20][C:21]([O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)=[CH:22][CH:23]=1)[CH3:17])(=[O:47])=[O:48]

Participants

7

Reactant 5

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 8471TriethylamineHCID 130462-Mesitylenesulfonyl chlorideHCID 105034IsocyanateHCID 22137316HCID 22137316, compound

Product 1

HCID 22137401HCID 22137401, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-(2-pyrrolid in-1-yl-ethoxy)-phenyl]-{1-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-ethyl}-amine (0.050 g, 0.12 mmol) in 0.4 mL methylene chloride was added triethylamine (0.05 mL, 0.36 mmol) and 2-mesitylenesulfonyl chloride (0.066 g, 0.30 mmol). The reaction mixture was stirred at room temperature for 3 days. PS-isocyanate resin (0.050 g) and PS-trisamine resin (0.050 g) were added and the reaction mixture was stirred at room temperature for 45 minutes. The resin was filtered off with the aid of methylene chloride. The filtrate was concentrated to afford 0.071 g of the crude title compound of Step A which was used without further purification. MS 593.2 (M+1)+

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 45 minutes
  2. filtrationThe resin was filtered off with the aid of methylene chloride
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-304269347625410c9aa3bdd720095a54
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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