Tris(hydroxymethyl)aminomethane → HCID 22137332, compound

HRID 1827550Notes

Reaction equation

HRID 1827550 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.[Br:37][C:38]1[CH:43]=[CH:42][C:41]([S:44](Cl)(=[O:46])=[O:45])=[C:40]([O:48][C:49]([F:52])([F:51])[F:50])[CH:39]=1.[N-]=C=O.C(O)C(N)(CO)CO>C(Cl)Cl>[Br:37][C:38]1[CH:43]=[CH:42][C:41]([S:44]([N:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:10][CH:11]=2)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)[CH:18]=2)(=[O:46])=[O:45])=[C:40]([O:48][C:49]([F:51])([F:50])[F:52])[CH:39]=1

Participants

7

Reactant 5

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 8471TriethylamineHCID 105034IsocyanateHCID 27364214-Bromo-2-(Trifluoromethoxy)Benzene-1-Sulfonyl ChlorideHCID 22137433[4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-amine

Product 1

HCID 22137332HCID 22137332, compoundYield 101%

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 (0.060 g, 0.15 mmol) in 0.4 mL methylene chloride was added triethylamine (0.06 mL, 0.45 mmol) and 4-bromo-2-trifluoromethoxybenzenesulfonyl chloride (0.103 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 afford the title compound of Step A (0.106 g). MS 700.8 (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-2834787f09ad4bec8564df820a33f084
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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