Tris(hydroxymethyl)aminomethane → HCID 22137421, compound

HRID 1827559Notes

Reaction equation

HRID 1827559 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]=[CH:19][C:18]=3[O:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:37]1([CH3:49])[CH:42]=[C:41]([CH3:43])[CH:40]=[C:39]([CH3:44])[C:38]=1[S:45](Cl)(=[O:47])=[O:46].[N-]=C=O.C(O)C(N)(CO)CO>C(Cl)Cl>[CH3:49][C:37]1[CH:42]=[C:41]([CH3:43])[CH:40]=[C:39]([CH3:44])[C:38]=1[S:45]([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][CH:20]=[CH:19][C:18]=1[O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1)(=[O:46])=[O:47]

Participants

7

Reactant 5

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 8471TriethylamineHCID 130462-Mesitylenesulfonyl chlorideHCID 105034IsocyanateHCID 22137446HCID 22137446, compound

Product 1

HCID 22137421HCID 22137421, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-[2-(tetrahydro-pyran-2-yloxy)-benzyl]-amine (0.060 g, 0.19 mmol) in 0.4 mL methylene chloride was added triethylamine (0.06 mL, 0.43 mmol) and 2-mesitylene sulfonyl chloride (0.066 g, 0.30 mmol). The reaction mixture was stirred at room temperature for 24 hr. PS-isocyanate resin (0.050 g), PS-trisamine resin (0.050 g), and 1.5 mL methylene chloride were added and the mixture was stirred for 2 hr. at room temperature. The resin was filtered off with the aid of methylene chloride. The filtrate was concentrated. The residue was purified by preparative TLC (1.0 mm silica gel layer, eluting with 10% methanol/methylene chloride) to afford the title compound of Step A (0.039 g). MS 579.3 (M+1)+

Workup

  1. stirringthe 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
  5. customThe residue was purified by preparative TLC (1.0 mm silica gel layer, eluting with 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-12123191292a43b2bf71c1fa0c8e09a0
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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