Tris(hydroxymethyl)aminomethane → HCID 22137402, compound

HRID 1827543Notes

Reaction equation

HRID 1827543 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[O:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][O:26]1)[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:9][CH:8]=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:6]([CH2:5][C:4]1[CH:21]=[CH:22][C:23]([O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)=[C:2]([CH3:1])[CH:3]=1)[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:9][CH:8]=1)(=[O:47])=[O:48]

Participants

7

Reactant 5

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 8471TriethylamineHCID 130462-Mesitylenesulfonyl chlorideHCID 105034IsocyanateHCID 22137337HCID 22137337, compound

Product 1

HCID 22137402HCID 22137402, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-methyl-4-(tetrahydro-pyran-2-yloxy)-benzyl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine (0.062 g, 0.15 mmol) in 0.4 mL methylene chloride was added triethylamine (0.06 mL, 0.45 mmol) and 2-mesitylene sulfonyl chloride (0.066 g, 0.3 mmol). The reaction mixture was stirred at room temperature for 24 hr. PS-isocyanate resin (0.050 g) and PS-trisamine 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 give the title compound of Step A (0.089 g). MS 593.3 (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-d2ad0e48547e4362abd6ae96148b02a2
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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